928-90-5

Basic information

• Product Name: 5-HEXYN-1-OL
• Synonyms: 1-Hydroxy-5-hexyne;5-hexyn-1-0l;6-Hydroxy-1-hexyne;Hex-5-yn-1-ol;5-HEXYN-1-OL;5-Hexyn-1-ol, 98 %;5-Hexyn-1-ol,97%;5-HEXYN-1-OL 98%
• CAS NO: 928-90-5
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Organic Building Blocks;Terminal
• Mol File: 928-90-5.mol
• Article Data: 28

Chemical Properties

• Melting Point: -34°C (estimate)
• Boiling Point: 73-75 °C15 mm Hg(lit.)
• Flash Point: 158 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 0.89 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.572mmHg at 25°C
• Refractive Index: n20/D 1.450(lit.)
• Storage Temp.: Refrigerator
• PKA: 15.05±0.10(Predicted)
• Water Solubility: Slightly miscible with water.
• BRN: 1739774
• CAS DataBase Reference: 5-HEXYN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HEXYN-1-OL(928-90-5)
• EPA Substance Registry System: 5-HEXYN-1-OL(928-90-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 928-90-5(Hazardous Substances Data)

Usage

Uses

5-Hexyn-1-ol is used as starting material for the preparation of terminal alkynes and lactones containing terminal alykyne groups. It is also used in the synthesis of cinnoline-fused cyclic enediyne, llycopodium alkaloids, (+)-nankakurine A and (+)-nankakurine B and 7-benzoyloxy-3-(2-nitrophenylseleno)-1,5-cyclodecadiyne.

InChI:InChI=1/C6H10O/c1-2-3-4-5-6-7/h1,7H,3-6H2

Synthetic route

tert-butyldimethylsilyl hex-5-yn-1-yl ether (73448-13-2) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With hydrogenchloride In methanol; water at 23℃; for 1h; Inert atmosphere;	93%
With triethylamine hydrofluoride In tetrahydrofuran at 50℃; for 19h; var. reag.: (n-Bu)4N(1+)*F(1-);	86%

2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran (1720-37-2) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With ammonium nitrate; Montmorillonite-K10 for 0.0583333h; deprotection; microwave irradiation;	86%
With ethanol; pyridinium p-toluenesulfonate at 55℃; var. reag.: TsOH, MeOH, 25 deg C, 7 h;	73%
With pyridinium p-toluenesulfonate In ethanol at 25℃; for 3h;

2-(chloromethyl)tetrahydropyran (18420-41-2, 130233-13-5, 130233-14-6) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With sodium amide; ferric nitrate In ammonia Whiting's double elimination;	85%
With sodium amide In ammonia	83%
With Iron(III) nitrate nonahydrate; ammonia; sodium for 4h; Cooling;	67%

hex-5-ynoic acid (53293-00-8) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 15h; Inert atmosphere;	82%
With LiAlH4 In diethyl ether

1-((hex-5-yn-1-yloxy)methyl)-4-methoxybenzene (123186-35-6) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane at 20℃; for 0.833333h;	80%
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite at 20℃; for 18h; Green chemistry; chemoselective reaction;	72%

hex-2-yn-1-ol (764-60-3) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With sodium hydride; ethylenediamine In mineral oil at 0 - 70℃;	52%
With sodium amide In various solvent(s)
With potassium tert-butylate; lithium; Trimethylenediamine at 20℃; Zipper reaction; Inert atmosphere;

methyl hex-5-ynoate (77758-51-1) + allyl-trimethyl-silane (762-72-1) → non-1-en-8-yn-4-ol + 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With indium (III) iodide; Dimethylphenylsilane In dichloromethane at 20℃; for 1.66667h; Inert atmosphere; chemoselective reaction;	A 40% B 22 %Spectr.

nitrite d'hexyne-5 ol-1 (77566-25-7) → 5-hexyl-1-ol (928-90-5) + 5-hexynal (29329-03-1) + (hydroxy-3 propyl)-3 isoxazole (77566-35-9)

Conditions	Yield
In benzene at 10 - 20℃; for 26h; Irradiation;	A 17% B 5% C 11%

3-hexyn-1-ol (1002-28-4) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With propane-1,3-diamine potassium salt

5-hexyn-1-yl acetate (68274-83-9) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With potassium hydroxide In methanol Heating;

hex-5-ynyloxy-trimethyl-silane (17889-21-3) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With sulfuric acid

methyl hex-5-ynoate (77758-51-1) → 5-hexyl-1-ol (928-90-5)

2-(chloromethyl)tetrahydropyran (18420-41-2, 130233-13-5, 130233-14-6) + ammonia (7664-41-7) + sodium → 5-hexyl-1-ol (928-90-5)

1-chloro-4-tetrahydropyranyloxybutane (41302-05-0) + lithium acetylide-ethylenediamine complex → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
Yield given. Multistep reaction;

Tetrahydropyran-2-methanol (100-72-1) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
Stage #1: Tetrahydropyran-2-methanol With pyridine; thionyl chloride Stage #2: With ammonia; sodium amide Further stages.;
Multi-step reaction with 2 steps 1: 65 percent / SOCl2 / pyridine / 8 h / 45 °C 2: 85 percent / NaNH2 / Fe(NO3)3*9H2O / liquid ammonia View Scheme
Multi-step reaction with 2 steps 1: SOCl2 / pyridine 2: Na / liquid ammonia View Scheme

1-phenylbut-1-en-3-yne (5622-76-4) + 6-bromo-hex-5-yn-1-ol (69284-62-4) → 5-hexyl-1-ol (928-90-5) + 10-phenyldec-9-ene-5,7-diyn-1-ol

Conditions	Yield
With hydroxylamine hydrochloride; isopropylamine; copper(l) chloride In ethanol for 18h; Inert atmosphere;

1-(tert-butyldiphenylsilyloxy)-5-hexyne (128217-23-2) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); sulfuric acid; water In methanol at 20℃; for 24h; Inert atmosphere;

1-(tert-butyldiphenylsilyloxy)-5-hexyne (128217-23-2) → 5-hexyl-1-ol (928-90-5) + 6-(tert-butyldiphenylsilyloxy)hexan-2-one (123171-29-9)

Conditions	Yield
With 2-dicyclohexyl(2′,6′-dimethoxybiphenyl)phosphine gold(I)bis(trifluoromethanesulfonyl)imide; water In methanol at 20℃; Inert atmosphere;	A 15 %Chromat. B 85 %Chromat.

5,6-dibromohexan-1-ol (18343-91-4) → 5-hexyl-1-ol (928-90-5) + 5-bromohex-5-en-1-ol (69441-76-5)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 40℃; for 24h; Reflux;

5-hydroxypentanal (4221-03-8) + dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 5.5h; Seyferth-Gilbert Homologation;

valeric acid (13392-69-3) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 6 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C 3: potassium carbonate / methanol / 5.5 h / 20 °C View Scheme

5-hydroxy-N,O-dimethyl-pentanohydroxamic acid (187756-41-8) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C 2: potassium carbonate / methanol / 5.5 h / 20 °C View Scheme

1 ,5-pentanediol (111-29-5) → 5-hexyl-1-ol (928-90-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 3.17 h / -78 - 23 °C / Inert atmosphere 2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hydrogencarbonate / dichloromethane; water / 0 °C / Inert atmosphere 2.2: 0.25 h / 0 - 23 °C / Inert atmosphere 3.1: triphenylphosphine / dichloromethane / 3.17 h / 0 - 23 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 23 °C / Inert atmosphere 5.1: hydrogenchloride / water; methanol / 1 h / 23 °C / Inert atmosphere View Scheme

5-(tert-butyldimethyl-silyloxy)pentan-1-ol (83067-20-3) → 5-hexyl-1-ol (928-90-5)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hydrogencarbonate / dichloromethane; water / 0 °C / Inert atmosphere 1.2: 0.25 h / 0 - 23 °C / Inert atmosphere 2.1: triphenylphosphine / dichloromethane / 3.17 h / 0 - 23 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 23 °C / Inert atmosphere 4.1: hydrogenchloride / water; methanol / 1 h / 23 °C / Inert atmosphere View Scheme

5-tert-butyldimethylsilyloxypentanal (87184-80-3) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: triphenylphosphine / dichloromethane / 3.17 h / 0 - 23 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 23 °C / Inert atmosphere 3: hydrogenchloride / water; methanol / 1 h / 23 °C / Inert atmosphere View Scheme

1,1-dibromo-6-(tert-butyldimethylsiloxy)hex-1-ene (306734-44-1) → 5-hexyl-1-ol (928-90-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 23 °C / Inert atmosphere 2: hydrogenchloride / water; methanol / 1 h / 23 °C / Inert atmosphere View Scheme

3,4-dihydro-2H-pyran (110-87-2) + 5-hexyl-1-ol (928-90-5) → 2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran (1720-37-2)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 1.25h;	100%
With water; sodium hydrogencarbonate; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt	98%
toluene-4-sulfonic acid In dichloromethane	98%

chloro-trimethyl-silane (75-77-4) + 5-hexyl-1-ol (928-90-5) → 6-trimethylsilanyl-hex-5-yn-1-ol (103437-52-1)

Conditions	Yield
Stage #1: 5-hexyl-1-ol With ethylmagnesium bromide Stage #2: chloro-trimethyl-silane Stage #3: With sulfuric acid In tetrahydrofuran	100%
Stage #1: 5-hexyl-1-ol With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78 - 0℃; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; Inert atmosphere;	100%
Stage #1: 5-hexyl-1-ol With dmap; n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane at -78 - 20℃; for 2h; Inert atmosphere;	99%

5-hexyl-1-ol (928-90-5) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethylsilyl hex-5-yn-1-yl ether (73448-13-2)

Conditions	Yield
With dmap; triethylamine In dichloromethane for 20h; Ambient temperature;	100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere;	100%
With 1H-imidazole; dmap In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

5-hexyl-1-ol (928-90-5) + methanesulfonyl chloride (124-63-0) → hex-5-ynyl methanesulphonate (79496-61-0)

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	100%
With triethylamine In diethyl ether at 0℃; for 3h;	99%
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;	98%

5-hexyl-1-ol (928-90-5) + trimethylaluminum (75-24-1) → 5-methylhex-5-en-1-ol (5212-80-6)

Conditions	Yield
With zirconocene dichloride In hexane; 1,2-dichloro-ethane at 20℃; for 22h; Addition;	100%

dibutyl disulfide (629-45-8) + 5-hexyl-1-ol (928-90-5) → (Z)-1,2-bis(butylthio)-1-hexen-6-ol

Conditions	Yield
With rhodium hydrido (PEt3)3 complex; trifluorormethanesulfonic acid; P(p-CH3OC6H4)3 In acetone for 10h; Heating;	100%

5-hexyl-1-ol (928-90-5) → (E)-6-iodo-5-hexen-1-ol (201035-80-5) + (Z)-6-iodo-5-hexene-1-ol (132716-07-5, 106335-91-5)

Conditions	Yield
Stage #1: 5-hexyl-1-ol With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 3.5h; Heating; Stage #2: With iodine In dichloromethane at 0℃; for 1.3h; Title compound not separated from byproducts;	A 100% B n/a
Multi-step reaction with 2 steps 1: 2,2'-azobis(isobutyronitrile) / tetrahydrofuran / 14 h / 80 - 90 °C / Inert atmosphere 2: iodine / dichloromethane / 14 h / 80 - 90 °C / Inert atmosphere View Scheme

5-hexyl-1-ol (928-90-5) + benzoyl chloride (98-88-4) → 6-benzoyloxy-1-hexyne (216064-35-6)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 1h;	100%
With dmap; triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In dichloromethane at 0 - 20℃;	99%

4-(4-bromophenyl)-3-butyn-1-ol (59099-79-5) + 5-hexyl-1-ol (928-90-5) → 6-(4-(4-hydroxy-1-butynyl)phenyl)-5-hexyn-1-ol (857349-14-5)

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 50℃; Sonogashira reaction;	100%

4-(4-bromophenyl)-4-pentyn-1-ol (857349-11-2) + 5-hexyl-1-ol (928-90-5) → 6-(4-(5-hydroxy-1-pentynyl)phenyl)-5-hexyn-1-ol (857349-13-4)

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 50℃; Sonogashira reaction;	100%

5-hexyl-1-ol (928-90-5) + para-iodoanisole (696-62-8) → 4-(6-hydroxy-hex-1-ynyl)-methoxybenzene (128599-33-7)

Conditions	Yield
Stage #1: 5-hexyl-1-ol; para-iodoanisole With copper(l) iodide; N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran for 1h; Sonogashira coupling; Stage #2: bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 12h;	100%
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;	96%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 2.5h;	94%

5-hexyl-1-ol (928-90-5) + 4-tolyl iodide (624-31-7) → 6-(p-tolyl)hex-5-yn-1-ol

Conditions	Yield
Stage #1: 4-tolyl iodide With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 0.166667h; Stage #2: 5-hexyl-1-ol at 20℃;	100%
With C24H28Cl2N2PPd; tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 110℃; for 6h; Sonogashira Cross-Coupling; Inert atmosphere;	96%
With potassium phosphate; copper(l) iodide; (E)-1,1-diphenyl-2-(pyridin-2-ylmethylene)hydrazine; dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 70℃; for 5h; Sonogashira cross-coupling;	73%

5-hexyl-1-ol (928-90-5) + isobutene (115-11-7) → tert-butyl 5-hexynyl ether (121587-75-5)

Conditions	Yield
With Amberlyst In hexane at 20℃; for 14h; Inert atmosphere;	100%

5-hexyl-1-ol (928-90-5) + 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (170011-47-9) → 6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)hex-5-yn-1-ol

Conditions	Yield
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;	100%

5-hexyl-1-ol (928-90-5) + ((3aS,4R,7R,7aS)-7-(3-azidopropyl)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methyl ((tert-butoxycarbonyl)leucyl)sulfamate → ((3aS,4R,7R,7aS)-7-(3-(4-(4-hydroxybutyl)-1H-1,2,3-triazol-1-yl)propyl)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methyl ((tert-butoxycarbonyl)leucyl)sulfamate

Conditions	Yield
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	100%

5-hexyl-1-ol (928-90-5) + 4-methoxy-benzoyl chloride (100-07-2) → 1-((hex-5-yn-1-yloxy)methyl)-4-methoxybenzene (123186-35-6)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere;	100%

5-hexyl-1-ol (928-90-5) + 6-azidohexan-1-ol (146292-90-2) → 6-(4-(4-hydroxybutyl)-1H-1,2,3-triazol-1-yl)hexan-1-ol (1240924-00-8)

Conditions	Yield
With polyvinylpyrrolidone coated copper(I) oxide nanoparticles In water at 37℃; for 48h; Sonication;	99.8%

5-hexyl-1-ol (928-90-5) + p-toluenesulfonyl chloride (98-59-9) → 5-hexynyl p-toluenesulfonate (76911-01-8)

Conditions	Yield
With pyridine at 0℃; for 16h;	99%
With 1-methyl-1H-imidazole; triethylamine In toluene at 20℃; for 1h; Cooling with ice;	99.7%
With pyridine at 0℃; for 6h;	98%

5-hexyl-1-ol (928-90-5) → 6-bromo-1-hexyne (66977-99-9)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere;	99%
With bromine; triphenylphosphine In acetonitrile at 0℃;	87%
With carbon tetrabromide; triphenylphosphine In diethyl ether for 1h; Ambient temperature;	65%

5-hexyl-1-ol (928-90-5) + acetic anhydride (108-24-7) → 5-hexyn-1-yl acetate (68274-83-9)

Conditions	Yield
With pyridine at 20℃; for 3h;	99%
With pyridine for 3h; Ambient temperature;	97%
With dmap; potassium carbonate In ethyl acetate	95%

5-hexyl-1-ol (928-90-5) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-(tert-butyldiphenylsilyloxy)-5-hexyne (128217-23-2)

Conditions	Yield
Stage #1: 5-hexyl-1-ol With 1H-imidazole In dichloromethane at 0℃; for 0.166667h; Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 0 - 20℃; for 17h;	99%
With 1H-imidazole In tetrahydrofuran at 20℃;	96%
With 1H-imidazole In tetrahydrofuran at 20℃; for 2h;	96%

iodobenzene (591-50-4) + 5-hexyl-1-ol (928-90-5) → 6-phenylhex-5-yn-1-ol (69936-53-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 12h; Inert atmosphere;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 18h; Inert atmosphere;	99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In tetrahydrofuran at 20℃;	98%

5-hexyl-1-ol (928-90-5) + benzyl bromide (100-39-0) → 1-benzyloxy-5-hexyne (60789-55-1)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Schlenk technique; Inert atmosphere;	99%
Stage #1: 5-hexyl-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 90h;	99%
With tetra-(n-butyl)ammonium iodide; potassium hydride In tetrahydrofuran at 0 - 25℃; Inert atmosphere;	97%

5-hexyl-1-ol (928-90-5) + p-methoxybenzyl chloride (824-94-2) → 1-((hex-5-yn-1-yloxy)methyl)-4-methoxybenzene (123186-35-6)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 18h; Inert atmosphere;	99%
With sodium hydride In mineral oil	99%
Stage #1: 5-hexyl-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 20℃; for 24h; Inert atmosphere;	91%

5-hexyl-1-ol (928-90-5) + o-nitroiodobenzene (609-73-4) → 2-(6-hydroxy-1-hexynyl)nitrobenzene (442155-84-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira coupling;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 13h; Sonogashira coupling;	99%
Stage #1: 5-hexyl-1-ol; o-nitroiodobenzene With bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine In N,N-dimethyl-formamide for 0.5h; Sonogashira coupling; Inert atmosphere; Stage #2: With copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 5.16667h; Sonogashira coupling; Inert atmosphere;	71%

p-nitrobenzene iodide (636-98-6) + 5-hexyl-1-ol (928-90-5) → (Z)-6-(4-nitrophenyl)-5-hexen-1-ol

Conditions	Yield
Stage #1: 5-hexyl-1-ol With triethyl borane; dichloroindium hydride In tetrahydrofuran; hexane at -78℃; for 2.5h; Stage #2: p-nitrobenzene iodide With 1,3-dimethyl-2-imidazolidinone; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trifuran-2-yl-phosphane In tetrahydrofuran; hexane for 0.5h; Heating;	99%
Stage #1: 5-hexyl-1-ol With indium(III) chloride; triethyl borane; diisobutylaluminium hydride In tetrahydrofuran; hexane at -78℃; for 2.5h; Stage #2: p-nitrobenzene iodide With trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran; hexane at 66℃; for 0.5h; Further stages.;	99%

5-hexyl-1-ol (928-90-5) + 2-iodochlorobenzene (615-41-8) → 6-(2-chloro-phenyl)-hex-5-yn-1-ol (608130-99-0)

Conditions	Yield
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 84℃; for 6h; Sonogashira coupling;	99%

5-hexyl-1-ol (928-90-5) + 3-methoxy-1-iodobenzene (766-85-8) → (Z)-6-(3-methoxyphenyl)-5-hexen-1-ol

Conditions	Yield
Stage #1: 5-hexyl-1-ol With indium(III) chloride; triethyl borane; diisobutylaluminium hydride In tetrahydrofuran; hexane at -40℃; for 2.5h; Stage #2: 3-methoxy-1-iodobenzene With trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran; hexane at 66℃; for 0.5h; Further stages.;	99%

iodobenzene (591-50-4) + 5-hexyl-1-ol (928-90-5) → 4-{1-phenyl-[1,2,3]triazol-4-yl}butan-1-ol

Conditions	Yield
With sodium azide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium L-ascorbate; copper(l) iodide In dimethyl sulfoxide at 20℃; for 1.5h;	99%

triisopropylsilyl chloride (13154-24-0) + 5-hexyl-1-ol (928-90-5) → 6-(triisopropyl-silanyl)hex-5-yn-1-ol (290813-10-4)

Conditions	Yield
Stage #1: 5-hexyl-1-ol With ethylmagnesium bromide In tetrahydrofuran for 8h; Heating; Stage #2: triisopropylsilyl chloride In tetrahydrofuran for 18h; Heating; Further stages.;	99%
Stage #1: 5-hexyl-1-ol With ethylmagnesium chloride In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; Stage #2: triisopropylsilyl chloride In tetrahydrofuran for 4h; Inert atmosphere; Reflux;	85%
Stage #1: 5-hexyl-1-ol With ethylmagnesium chloride In tetrahydrofuran for 16h; Heating; Stage #2: triisopropylsilyl chloride In tetrahydrofuran for 6h; Heating;	80%

Upstream product

• 18420-41-2 2-(chloromethyl)tetrahydropyran 
• 77758-51-1 methyl hex-5-ynoate 
• 7664-41-7 ammonia 
• 41302-05-0 1-chloro-4-tetrahydropyranyloxybutane 
• 5622-76-4 1-phenylbut-1-en-3-yne 
• 69284-62-4 6-bromo-hex-5-yn-1-ol 
• 128217-23-2 1-(tert-butyldiphenylsilyloxy)-5-hexyne 
• 18343-91-4 5,6-dibromohexan-1-ol 
• 123186-35-6 1-[(hex-5-yn-1-yloxy)methyl]-4-methoxybenzene 
• 306734-44-1 1,1-dibromo-6-(tert-butyldimethylsiloxy)hex-1-ene 
• 87184-80-3 5-tert-butyldimethylsilyloxypentanal 
• 83067-20-3 5-(tert-butyldimethyl-silyloxy)pentan-1-ol 
• 111-29-5 1 ,5-pentanediol 
• 187756-41-8 5-hydroxy-pentanoic acid methyl-methoxy-amide 

Downstream Products

• 53293-00-8 hex-5-ynoic acid 
• 68274-97-5 dec-5-yn-1-ol 
• 41547-21-1 5-octyn-1-ol 
• 64275-59-8 (E)-10-pentadecen-5-yn-1-ol 
• 64275-55-4 (Z)-10-Pentadecen-5-in-1-ol 
• 1720-37-2 2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 
• 190184-84-0 1,2-Benzoldicarbonsaeuremonohex-5-inylester 
• 72726-42-2 (E)-6-Chloro-5-phenylselanyl-hex-5-en-1-ol 
• 128599-33-7 4-(6-hydroxy-hex-1-ynyl)-methoxybenzene 
• 133446-39-6 methyl 2-(6-hydroxy-1-hexynyl)benzoate 
• 102356-83-2 4-[3-(4-chlorobenzoyl)isoxazol-5-yl]butan-1-ol 
• 102356-84-3 4-[3-(4-toluoyl)isoxazol-5-yl]butan-1-ol 
• 147972-99-4 Hex-5-ynyloxy-methyl-diphenyl-silane 
• 116488-01-8 (Z)-6-Triphenylgermanyl-hex-5-en-1-ol 

Relevant articles and documents

Synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide

Herein, a new protocol for rapid synthesis of α,β-unsaturated epoxy ketones utilizing a bifunctional sulfonium/phosphonium ylide is described. This approach comprises two sequential chemoselective reactions between sulfonium and phosphonium ylides and two distinct aldehydes, which allows for the rapid construction of a variety of unsymmetric α,β-unsaturated epoxy ketones. This methodology allows the rapid construction of the core reactive functionality of a family of lipid peroxidation products, the epoxyketooctadecenoic acids, but can be further broadly utilized as a useful synthon for the synthesis of natural products, particularly those derived from oxidized fatty acids. Accordingly, a protocol utilizing this approach to synthesize the epoxyketooctadecenoic acid family of molecules is described.

Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides

Herein, we report on the first enantioselective and atom-efficient catalytic one-step dimerization method to selectively transform ω-allenyl carboxylic acids into C2-symmetric 14- to 28-membered bismacrolactones (macrodiolides). This convenient asymmetric access serves as an attractive route towards multiple naturally occuring homodimeric macrocyclic scaffolds and demonstrates excellent efficiency to construct the complex, symmetric core structures. By utilizing a rhodium catalyst with a modified chiral cyclopentylidene-diop ligand, the desired diolides were obtained in good to high yields, high diastereoselectivity, and excellent enantioselectivity.

Synthesis and solid-state polymerization of a macrocyclic compound with two butadiyne units

A macrocyclic compound 1 with two butadiyne and four dodecyloxy-substituted benzamide moieties was successfully synthesized, and its ring structure was confirmed by the MALDI-TOF mass spectra and the 1HNMR spectra. Compound 1 showed two modifications depending on solvent for the solidification. Characteristic excitonic absorption bands of polydiacetylene were observed at around 500 nm for one of the modifications after UV irradiation. Quantitative conversion of butadiyne moieties to the corresponding polydiacetylene structure was confirmed by the Raman spectra.