3623-15-2

Basic information

• Product Name: 1-Phenyl-2-propyn-1-one
• Synonyms: 3-oxo-3-phenylpropyne;1-PHENYLPROP-2-YN-1-ONE;1-Phenyl-2-propyn-1-one;1-Oxo-2-propynylbenzene;Benzoylacetylene;Propinoylbenzene;Propiolophenone;2-PROPYN-1-ONE,1-PHENYL
• CAS NO: 3623-15-2
• Molecular Formula: C₉H₆O
• Molecular Weight: 130.14
• Product Categories: Aromatics
• Mol File: 3623-15-2.mol
• Article Data: 109

Chemical Properties

• Melting Point: 50-51 °C
• Boiling Point: 213.7 °C at 760 mmHg
• Flash Point: 76.6 °C
• Appearance: /
• Density: 1.073g/cm³
• Vapor Pressure: 0.162mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: 2-8°C
• BRN: 606216
• CAS DataBase Reference: 1-Phenyl-2-propyn-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-2-propyn-1-one(3623-15-2)
• EPA Substance Registry System: 1-Phenyl-2-propyn-1-one(3623-15-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 3623-15-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 3658, 1990 DOI: 10.1021/jo00298a052Tetrahedron Letters, 36, p. 9117, 1995 DOI: 10.1016/0040-4039(95)01978-Q

InChI:InChI=1/C9H6O/c1-2-9(10)8-6-4-3-5-7-8/h1,3-7H

Synthetic route

1-Phenyl-2-propyn-1-ol (4187-87-5) → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With Jones reagent In acetone at 0℃; Jones Oxidation; Inert atmosphere;	100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 5h;	99%
With sodium hypochlorite pentahydrate; 4-acetamido-2,2,6,6-tetramethylpiperidine-N-hydroxyammonium tetrafluoroborate In water; acetonitrile at 20℃; for 0.75h;	99%

(E)-1-methoxy-4-(4-phenylbut-1-en-3-yn-1-yl)benzene (41790-90-3, 61172-18-7) → 4-methoxy-benzaldehyde (123-11-5) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin In chloroform Irradiation;	A 83% B 85%

(E)-1,4-Diphenylbut-1-en-3-yne (13343-79-8) → benzaldehyde (100-52-7) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin In chloroform for 75h; Irradiation;	A 80% B 84%

propargyl benzene (10147-11-2) → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With tert.-butylhydroperoxide; [copper(II)(salqu)] In acetonitrile at 70℃; for 4h;	77%
With tetrachloromethane; di-tert-butyl chromate; acetic acid Reagens 4: Acetanhydrid;
With selenium(IV) oxide; ethanol

bis(p-chlorophenyl) diselenide (20541-49-5) + 1-Phenyl-2-propyn-1-ol (4187-87-5) → (Z)-2-(4-Chloro-phenylselanyl)-3-phenyl-propenal (105423-64-1) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With sulfuric acid; tetraethylammonium perchlorate In water; acetonitrile at 65℃; for 14h; electrochemical oxidation;	A 74% B 12%

1,1-dichloro-3-ethoxy-3-phenylpropene (87406-35-7) → 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2) + (E)1-chloro-3,3-diethoxy-3-phenylpropene

Conditions	Yield
With sodium ethanolate In ethanol at 80℃; for 18h;	A 72% B n/a C 18% D 9%

benzaldehyde (100-52-7) + acetylenemagnesium bromide (4301-14-8) → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
Stage #1: benzaldehyde; acetylenemagnesium bromide In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #2: With chromium(VI) oxide; sulfuric acid In acetone at 0℃; for 3h; Inert atmosphere;	69%
Stage #1: benzaldehyde; acetylenemagnesium bromide Inert atmosphere; Stage #2: With Jones reagent Inert atmosphere;

ethanol (64-17-5) + 1,1,1,3-tetrachloro-3-phenylpropane (23691-27-2) → 1,1-dichloro-3-ethoxy-3-phenylpropene (87406-35-7) + 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With sodium ethanolate for 18h; Heating; Further byproducts given;	A 22% B 2% C 2% D 59%

1-phenyl-2-(1H-tetrazol-5-yl)ethanone (355116-17-5) → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With lead(IV) acetate In 1,4-dioxane at 0℃; for 0.5h;	53%

benzaldehyde (100-52-7) + trimethylsilylacetylene (1066-54-2) → 3-(trimethylsilyl)-1-phenyl-2-propyn-1-one (13829-77-1) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
Stage #1: trimethylsilylacetylene With indium(III) bromide; triethylamine In diethyl ether at 20℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: benzaldehyde In diethyl ether at 40℃; for 24h; Inert atmosphere; Sealed tube;	A 40% B 10%

ethanol (64-17-5) + 1,1,1,3-tetrachloro-3-phenylpropane (23691-27-2) → ethyl 3-phenyl-2-propenoate (103-36-6) + 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With potassium hydroxide for 18h; Heating; Further byproducts given;	A 2% B 33% C 5% D 14%

ethanol (64-17-5) + 1,1,1,3-tetrachloro-3-phenylpropane (23691-27-2) → 3-Oxo-3-phenylpropanal 1-(diethylacetal) (36234-10-3) + 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With potassium hydroxide for 18h; Heating; Further byproducts given;	A 2% B 33% C 5% D 14%

ethanol (64-17-5) + 1,1,1,3-tetrachloro-3-phenylpropane (23691-27-2) → phenylpropargyl aldehyde diethyl acetal (6142-95-6) + 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With potassium hydroxide for 18h; Heating; Further byproducts given;	A 8% B 33% C 5% D 14%

ethanol (64-17-5) + 1,1,1,3-tetrachloro-3-phenylpropane (23691-27-2) → 3-ethoxy-3-phenyl-2-propenal (60355-48-8) + 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With potassium hydroxide for 18h; Heating; Further byproducts given;	A 2% B 33% C 5% D 14%

ethanol (64-17-5) + 1,1,1,3-tetrachloro-3-phenylpropane (23691-27-2) → 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2) + (E)1-chloro-3,3-diethoxy-3-phenylpropene

Conditions	Yield
With potassium hydroxide for 18h; Heating; Further byproducts given;	A 33% B 5% C 14% D 3%

1,1,1,3-tetrachloro-3-phenylpropane (23691-27-2) → 1-phenyl-propynone-diethylacetal (87406-33-5) + (Z)-β-chloro-1-phenyl propenone (15724-79-5) + phenyl propargyl ketone (3623-15-2) + (E)1-chloro-3,3-diethoxy-3-phenylpropene

Conditions	Yield
With potassium hydroxide In ethanol for 18h; Heating; Further byproducts given;	A 33% B 5% C 14% D 3%

1-Phenyl-2-propyn-1-ol (4187-87-5) → 3-phenyl-3-keto-propanol-di(1-phenyl-2-propyn-1-yl) acetal (86476-37-1) + phenyl propargyl ketone (3623-15-2)

Conditions	Yield
at 5℃; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.1M KOH/t-butanol - water (1:1);	A 28% B 4%
at 5℃; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: KOH/t-butanol - water (1:1);	A 28% B 4%

tetrachloromethane (56-23-5) + propargyl benzene (10147-11-2) + di-tert-butyl chromate (1189-85-1) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → phenyl propargyl ketone (3623-15-2)

3-(trimethylsilyl)-1-phenyl-2-propyn-1-one (13829-77-1) → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With borax
With borax In methanol
Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 2 h 2: chromium(VI) oxide; sulfuric acid / acetone; water / 0.33 h / 0 °C View Scheme

ethyl [2]alcohol (925-93-9) + 1,1-dichloro-3-ethoxy-3-phenylpropene (87406-35-7) → 1-phenyl-propynone-diethylacetal (87406-33-5) + 1-phenyl-3-deuterioprop-2-yn-1-one (81060-96-0) + phenyl propargyl ketone (3623-15-2) + (E)1-chloro-3,3-diethoxy-3-phenylpropene + C11H11(2)HCl2O + C13H16(2)HClO2

Conditions	Yield
With sodium ethanolate for 8h; Mechanism; Heating;

C9H5(3)HO (134817-20-2) → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With water; hydrogenphosphate In tetrahydrofuran at 25℃; Rate constant;

C21H33BN2O → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; hexane Ambient temperature; Yield given;

3,5,6,6-tetramethyl-3-(1-phenyl-3-methylsilanyl-1-trimethylsilanyloxyprop-2-ynyl)-3,6-dihydro[1,4]oxazin-2-one (245343-75-3) → phenyl propargyl ketone (3623-15-2) + 3,5,6,6-tetramethyl-3,6-dihydro-[1,4]oxazin-2-one (245343-67-3)

Conditions	Yield
With water; pyridinium p-toluenesulfonate Hydrolysis;

selenium(IV) oxide (7446-08-4) + ethanol (64-17-5) + propargyl benzene (10147-11-2) → phenyl propargyl ketone (3623-15-2)

benzaldehyde (100-52-7) + Fmoc-L-tert-leucine on Wang resin → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C 2: IBX / ethyl acetate; tetrahydrofuran / 80 °C View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C 2: IBX / ethyl acetate / 80 °C View Scheme

benzaldehyde (100-52-7) + (E)-n-C6H13CH=CHZrCp2Cl → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: MnO2 / CH2Cl2 / 20 °C View Scheme

benzoic acid methyl ester (93-58-3) + α-methoxy-phenylacetic acid → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / NaH / tetrahydrofuran / Heating 2: 86 percent / NaN3; AlCl3 / tetrahydrofuran / 5 h / Heating 3: 53 percent / Pb(OAc)4 / dioxane / 0.5 h / 0 °C View Scheme

Benzoylacetonitrile (614-16-4) → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / NaN3; AlCl3 / tetrahydrofuran / 5 h / Heating 2: 53 percent / Pb(OAc)4 / dioxane / 0.5 h / 0 °C View Scheme

benzoyl chloride (98-88-4) + (+-)-<4-isopropyl-benzylamino>-phenyl-acetonitrile → phenyl propargyl ketone (3623-15-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 2: 3N HCl / tetrahydrofuran; hexane / Ambient temperature View Scheme

((S)-1-carbamimidoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (872459-79-5) + phenyl propargyl ketone (3623-15-2) → [(S)-2-phenyl-1-(4-phenyl-pyrimidin-2-yl)-ethyl]-carbamic acid tert-butyl ester (872459-80-8)

Conditions	Yield
With sodium carbonate In acetonitrile at 120℃; for 0.666667h; Microwave irradiation;	100%

pyridinium tetrafluoroborate + phenyl propargyl ketone (3623-15-2) → C14H12NO(1+)*BF4(1-)

Conditions	Yield
In methanol at 65℃;	100%

(1Z,4RS,5RS)-4-(benzoylamino)-5-phenyl-1-(3,4,5-trimethoxybenzylidene)pyrazolidin-3-on-1-azomethine imine + phenyl propargyl ketone (3623-15-2) → rac-N-((1S,6R,7R)-2-benzoyl-5-oxo-7-phenyl-1-(3,4,5-trimethoxyphenyl)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-6-yl)benzamide

Conditions	Yield
With copper In dichloromethane at 20℃; stereoselective reaction;	100%

phenyl propargyl ketone (3623-15-2) + N-methyl-p-toluenesulfonylamide (640-61-9) → (E)-N,4-dimethyl-N-(3-oxo-3-phenylprop-1-en-1-yl)benzenesulfonamide

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; water at 20℃; Inert atmosphere;	100%
With potassium carbonate In tetrahydrofuran at 80℃; Inert atmosphere;	80%

phenylmethanethiol (100-53-8) + phenyl propargyl ketone (3623-15-2) → 3,3-bis(benzylmercapto)propiophenone (74896-60-9)

Conditions	Yield
With tributylphosphine In tetrahydrofuran	99%
With 1-butyl-3-methylimidazolium hydroxide; 1-n-butyl-3-methylimidazolim bromide for 0.333333h;	95%

benzamidine monohydrochloride (1670-14-0) + phenyl propargyl ketone (3623-15-2) → 2,4-diphenylpyrimidine (25095-48-1)

Conditions	Yield
With sodium carbonate In acetonitrile at 120℃; for 0.666667h; microwave irradiation;	99%
With sodium carbonate In acetonitrile at 120℃; for 0.666667h; Microwave irradiation;	98%

3,5-dimethoxyphenol (500-99-2) + phenyl propargyl ketone (3623-15-2) → chrysinidin dimethylether hexafluorophosphate

Conditions	Yield
With hexafluorophosphoric acid In acetic acid at 20℃; for 48h;	99%
With hexafluorophosphoric acid In acetic acid at 20℃;	99%

C14H9NOS (161952-32-5) + phenyl propargyl ketone (3623-15-2) → C23H15NO2S (1253801-90-9)

Conditions	Yield
With triphenylphosphine In toluene at 20℃; Inert atmosphere; regioselective reaction;	99%

2-benzoyl-3-phenylacrylonitrile (20413-05-2) + phenyl propargyl ketone (3623-15-2) → C25H17NO2 (1253801-70-5)

Conditions	Yield
With triphenylphosphine In acetonitrile at 20℃; Inert atmosphere; regioselective reaction;	99%

2-benzoyl-3-(2-furyl)prop-2-enenitrile (61222-94-4) + phenyl propargyl ketone (3623-15-2) → C23H15NO3 (1253801-80-7)

Conditions	Yield
With triphenylphosphine In toluene at 20℃; Inert atmosphere; regioselective reaction;	99%

phenyl propargyl ketone (3623-15-2) + (E)-2-Benzoyl-3-(4-bromo-phenyl)-acrylonitrile → C25H16BrNO2 (1253801-82-9)

Conditions	Yield
With triphenylphosphine In toluene at 20℃; Inert atmosphere; regioselective reaction;	99%

phenyl propargyl ketone (3623-15-2) + 3-phenyloxindole (3456-79-9, 123742-97-2) → C23H17NO2

Conditions	Yield
With C35H52N4O4; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; dichloromethane at 30℃; for 5h; Michael Addition; Molecular sieve; enantioselective reaction;	99%

3-(4-fluorophenyl)indolin-2-one (282549-48-8) + phenyl propargyl ketone (3623-15-2) → C23H16FNO2

Conditions	Yield
With C35H52N4O4; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; dichloromethane at 30℃; for 3h; Michael Addition; Molecular sieve; enantioselective reaction;	99%

3-(m-tolyl)indolin-2-one (1255502-42-1) + phenyl propargyl ketone (3623-15-2) → C24H19NO2

Conditions	Yield
With C35H52N4O4; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; dichloromethane at 30℃; for 5h; Michael Addition; Molecular sieve; enantioselective reaction;	99%

3-(naphthalen-2-yl)indolin-2-one (1235862-81-3) + phenyl propargyl ketone (3623-15-2) → C27H19NO2

Conditions	Yield
With C35H52N4O4; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; dichloromethane at 30℃; for 5h; Michael Addition; Molecular sieve; enantioselective reaction;	99%

aminomalonic acid diethyl ester (6829-40-9) + 1-benzyl-7-fluoroindoline-2,3-dione (1190109-45-5) + phenyl propargyl ketone (3623-15-2) → (S)-diethyl 3'-benzoyl-1-benzyl-7-fluoro-2-oxospiro[indoline-3,2'-pyrrole]-5',5'(1'H)-dicarboxylate

Conditions	Yield
With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 25℃; for 36h; Molecular sieve; enantioselective reaction;	99%

N-hydroxyphthalimide (524-38-9) + phenyl propargyl ketone (3623-15-2) → 3-benzoyl-3a-hydroxy-3aH-1-oxa-8a-azacyclopenta[a]indene-8-one (1447925-07-6)

Conditions	Yield
With triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	99%
With triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 1h;	99%

C14H15Cl2NO4 + phenyl propargyl ketone (3623-15-2) → diethyl 4-benzoyl-5-(3,4-dichlorophenyl)-1H-pyrrole-2,2(5H)-dicarboxylate (1325732-02-2)

Conditions	Yield
With (S,Sp)-R-Phosferrox; copper(II) acetate monohydrate; triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Molecular sieve; enantioselective reaction;	99%

tert-butyl (E)-oct-2-en-1-yl-L-prolinate + phenyl propargyl ketone (3623-15-2) → (R)-2-benzoyl-7a-((S)-oct-1-en-3-yl)-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one

Conditions	Yield
In acetonitrile at 20℃; for 72h; Inert atmosphere; Darkness; enantioselective reaction;	99%

tert-butyl allyl-L-prolinate + phenyl propargyl ketone (3623-15-2) → (R)-7a-allyl-2-benzoyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one

Conditions	Yield
In acetonitrile at 60℃; for 48h; Inert atmosphere; Darkness; enantioselective reaction;	99%

tert-butyl (E)-(3-(4-bromophenyl)allyl)-L-prolinate + phenyl propargyl ketone (3623-15-2) → (R)-2-benzoyl-7a-((R)-1-(4-bromophenyl)allyl)-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one

Conditions	Yield
In acetonitrile at 20℃; for 72h; Inert atmosphere; Darkness; enantioselective reaction;	99%

thiophenol (108-98-5) + phenyl propargyl ketone (3623-15-2) → 1-phenyl-3,3-bis(phenylthio)propan-1-one (42426-92-6)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydroxide; 1-n-butyl-3-methylimidazolim bromide for 0.25h;	98%
With lithium tert-butoxide In ethanol at 20℃; for 0.166667h;	88%
With sodium acetate In tetrahydrofuran; water at 70℃; for 2.5h;	80%
With N-benzyl-trimethylammonium hydroxide In methanol

phenyl propargyl ketone (3623-15-2) + 3-phenyl-4-amino-5-mercapto-1,2,4-triazole (22706-11-2) → 4-amino-3-(benzoylvinylthio)-5-phenyl-1,2,4-triazole (121033-63-4)

Conditions	Yield
In methanol at 20℃; for 3h;	98%
In methanol at 65℃; for 5h;	84%

phenyl propargyl ketone (3623-15-2) + ethanethiol (75-08-1) → β,β-diethylthioethyl phenyl ketone (74896-59-6)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydroxide; 1-n-butyl-3-methylimidazolim bromide for 0.333333h;	98%
In ammonia for 1h;	96%
With sodium acetate In tetrahydrofuran; water at 70℃; for 3h;	75%

phenyl propargyl ketone (3623-15-2) → 1,3,5-tribenzoylbenzene (25871-69-6)

Conditions	Yield
dmap; acetylacetone In dichloromethane at 20℃; for 2h;	98%
With t-butyl azide In 1,4-dioxane at 100℃; for 30h;	64.3%
In N,N-dimethyl-formamide for 3h; Heating;	57%

phenyl propargyl ketone (3623-15-2) → phenyl(1H-1,2,3-triazol-4-yl)methanone (5955-92-0)

Conditions	Yield
With sodium azide In N,N-dimethyl acetamide at 55℃; for 0.666667h; microwave irradiation;	98%
With sodium azide In N,N-dimethyl acetamide at 100℃; for 2h; Cycloaddition;	95%
With sodium azide In N,N-dimethyl acetamide at 20 - 100℃; for 14h; Cycloaddition;	95%

ethyl 3-aminobut-2-enoate (626-34-6) + phenyl propargyl ketone (3623-15-2) → ethyl 2-methyl-6-phenylnicotinate (1702-14-3)

Conditions	Yield
In acetic acid; toluene at 170℃; for 0.166667h; Product distribution; Further Variations:; Solvents; microwave irradiation; Bohlmann-Rahtz synthesis;	98%

acetoacetamido (5977-14-0) + phenyl propargyl ketone (3623-15-2) → 2-methyl-6-phenylpyridine-3-carboxamide

Conditions	Yield
With ammonium acetate In ethanol for 24h; Bohlmann-Rahtz reaction; Heating;	98%
With ammonium acetate In ethanol for 24h; Heating;	98%

ethane-1,2-dithiol (540-63-6) + phenyl propargyl ketone (3623-15-2) → 2-(1,3-dithiolan-2-yl)-1-phenylethan-1-one (5653-29-2)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydroxide; 1-n-butyl-3-methylimidazolim bromide for 0.25h;	98%
With sodium acetate In tetrahydrofuran; water at 70℃; for 3.5h;	74%

Upstream product

• 10147-11-2 propargyl benzene 
• 56-23-5 tetrachloromethane 
• 1189-85-1 di-tert-butyl chromate 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 13829-77-1 3-(trimethylsilyl)-1-phenyl-2-propyn-1-one 
• 64-17-5 ethanol 
• 23691-27-2 1,1,1,3-tetrachloro-3-phenylpropane 
• 925-93-9 ethyl [2]alcohol 
• 87406-35-7 1,1-dichloro-3-ethoxy-3-phenylpropene 
• 13343-79-8 (E)-1,4-Diphenylbut-1-en-3-yne 
• 41790-90-3 (E)-1-methoxy-4-(4-phenylbut-1-en-3-yn-1-yl)benzene 
• 134817-20-2 C₉H₅⁽³⁾HO 

Downstream Products

• 3506-37-4 (E)-1-phenyl-3-(piperidin-1-yl)prop-2-en-1-one 
• 4677-13-8 (E)-3-(2-methyl-1H-indol-3-yl)-1-phenylprop-2-en-1-one 
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Relevant articles and documents

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Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.

Multisubstituted pyrazole synthesis via [3?+?2] cycloaddition/rearrangement/N[sbnd]H insertion cascade reaction of α-diazoesters and ynones

The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)3 as the catalyst are described. A series of 4-substituted pyrazoles were obtained via [3 + 2] cycloaddition, 1,5-ester shift, 1,3-H shift, and N[sbnd]H insertion process. Deuterium labelling experiments, kinetic studies and control experiments were carried out for the rationalization of the mechanism.