1774-47-6

Basic information

• Product Name: Trimethylsulfoxonium iodide
• Synonyms: sulfonium,trimethyl-,iodide,oxide;Sulfoxonium,trimethyl-,iodide;trimethyl-sulfoxoniuiodide;trimethylsulphoxoniumioidie;RARECHEM AQ A1 0066;TRIMETHYLSULFOXONIUM IODIDE;TRIMETHYLSULPHOXONIUM IODIDE;TMSOI
• CAS NO: 1774-47-6
• Molecular Formula: C₃H₉OS*I
• Molecular Weight: 220.07
• EINECS: 217-204-2
• Product Categories: Iodonium Sulfonium & Oxonium Compounds;Sulfonium Compounds;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Sulfonium/Sulfoxonium Compounds;Organic Building Blocks;Sulfur Compounds;Sulfonium/Sulfoxonium Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Pharmaceutical Intermediates;Pyridines
• Mol File: 1774-47-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 208-212 °C (dec.)(lit.)
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.7074 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 50 mg/mL, clear
• Water Solubility: 15 g/L (20 ºC)
• Sensitive: Light Sensitive
• BRN: 3595854
• CAS DataBase Reference: Trimethylsulfoxonium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethylsulfoxonium iodide(1774-47-6)
• EPA Substance Registry System: Trimethylsulfoxonium iodide(1774-47-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36-24/25
• WGK Germany: 2
• RTECS: WS3585000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 1774-47-6(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO LIGHT YELLOW CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 1774-47-6 differently. You can refer to the following data:
1. Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5
2. Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides.
3. Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.

InChI:InChI=1/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1

Synthetic route

dimethyl sulfoxide (67-68-5) + methyl iodide (74-88-4) → trimethylsulfoxonium iodide (1774-47-6)

Conditions	Yield
at 70℃; for 48h;	65%
for 72h; Reflux;	60%
for 72h; Reflux;	60%

dimethyl sulfoxide (67-68-5) → Na4(triiodide)3I(dimethylsulfoxide)15 + trimethylsulfoxonium iodide (1774-47-6)

Conditions	Yield
Stage #1: dimethyl sulfoxide With water; sodium hydroxide at 20℃; for 0.5h; Ultrasonication; Stage #2: With methyl iodide at 20℃; for 144h; Ultrasonication;	A 28% B 13%

acetic anhydride (108-24-7) + 3-O-(β-D-galactopyranosyl)-D-arabinose (61272-23-9, 130767-77-0, 130767-78-1) + methyl iodide (74-88-4) → Ethyl methyl sulfoxide (1669-98-3) + 1,3,4-tri-O-acetyl-2,5-di-O-methyl-D-arabinitol (100758-68-7) + 1,5-di-O-acetyl-2,3,4,6-tetra-O-methyl-D-galactitol (19285-93-9, 19318-49-1, 20316-14-7, 25665-99-0, 53403-07-9, 81600-01-3, 83290-15-7, 103729-41-5, 114183-58-3, 25521-30-6) + 1,3,5-tri-O-acetyl-2,4-di-O-methyl-D-arabinitol (19318-22-0, 19318-27-5, 84885-38-1, 84925-47-3, 100758-67-6) + trimethylsulfoxonium iodide (1774-47-6)

Conditions	Yield
With sodium tetrahydroborate; perchloric acid; trimethylsulfoxonium iodide; trifluoroacetic acid In dimethyl sulfoxide Product distribution; Improved methylation analysis; other saccharides;

dimethyloxosulfonium methylide → trimethylsulfoxonium iodide (1774-47-6)

2-Adamantanone (700-58-3) + trimethylsulfoxonium iodide (1774-47-6) → 2-adamantanespiroxirane (24759-97-5)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol for 1h; Reflux;	100%
With sodium hydroxide In isopropyl alcohol for 1h; Heating;	85%
With potassium tert-butylate In 1,2-dimethoxyethane for 18h; Heating;	85%
With sodium hydride Corey-Chaykovsky epoxidation;	65%
Epoxidation;

1-phenylmethyl-4-piperidone (3612-20-2) + trimethylsulfoxonium iodide (1774-47-6) → N-benzyl-1-oxa-6-azaspiro[2,5]-octane (19867-34-6)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 10 - 20℃; for 1h; Stage #2: 1-phenylmethyl-4-piperidone In dimethyl sulfoxide; mineral oil at 20℃; for 1.5h;	100%
With tetrabutylammomium bromide; sodium hydroxide In toluene at 80℃; for 8h;	93%
Stage #1: trimethylsulfoxonium iodide With tetrabutylammomium bromide; sodium hydride In dimethyl sulfoxide at 0℃; for 1h; Stage #2: 1-phenylmethyl-4-piperidone In dimethyl sulfoxide at 20℃; for 1.5h; Reagent/catalyst; Time;	93%

4-Phenyl-2-butanone (2550-26-7) + trimethylsulfoxonium iodide (1774-47-6) → 2-methyl-2-phenethyloxirane (7065-28-3, 130284-36-5)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; Inert atmosphere;	100%
With potassium tert-butylate In dimethyl sulfoxide for 16h; Ambient temperature;	98%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 0.166667h; Johnson-Corey-Chaykovsky Reaction; Inert atmosphere; Stage #2: 4-Phenyl-2-butanone In dimethyl sulfoxide at 0 - 20℃; for 17h; Johnson-Corey-Chaykovsky Reaction; Inert atmosphere;	92%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In dimethyl sulfoxide at 22℃; for 0.5h; Stage #2: 4-Phenyl-2-butanone	71%

trimethylsulfoxonium iodide (1774-47-6) + 2-(5-bromopyridin-2-yl)-1-(2,4-difluorophenyl)-2,2-difluoroethanone (294182-06-2) → 5-bromo-2-((-2-(2,4-difluorophenyl)oxiran-2-yl)difluoromethyl)pyridine (294182-28-8)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 2-(5-bromopyridin-2-yl)-1-(2,4-difluorophenyl)-2,2-difluoroethanone In tetrahydrofuran at 0 - 2℃; for 2h; Temperature; Inert atmosphere;	100%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 10 - 20℃; for 1.5h; Stage #2: 2-(5-bromopyridin-2-yl)-1-(2,4-difluorophenyl)-2,2-difluoroethanone In tetrahydrofuran at -10℃; for 1h;	61%
Stage #1: trimethylsulfoxonium iodide With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 2-(5-bromopyridin-2-yl)-1-(2,4-difluorophenyl)-2,2-difluoroethanone In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 1h;	54.9%

Benzyloxymethyl-oxiran (2930-05-4) + trimethylsulfoxonium iodide (1774-47-6) → 2-((benzyloxy)methyl)oxetane (489427-99-8)

Conditions	Yield
With iron(III) chloride; potassium tert-butylate In tert-butyl alcohol at 80℃; for 3h; Reagent/catalyst; Inert atmosphere;	100%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tert-butyl alcohol at 50℃; for 1h; Stage #2: Benzyloxymethyl-oxiran In tert-butyl alcohol at 50℃; for 72h; Further stages.;	65%

trimethylsulfoxonium iodide (1774-47-6) + carbonic acid benzyl ester 4-dimethylamino-2-[2-ethyl-3,4,10-trihydroxy-13-(4-methoxy-4,6-dimethyl-5-oxo-tetrahydro-pyran-2-yloxy)-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-aza-cyclopentadec-11-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester (371193-61-2) → carbonic acid benzyl ester 4-dimethylamino-2-[2-ethyl-3,4,10-trihydroxy-13-(8-methoxy-4,8-dimethyl-1,5-dioxa-spiro[2.5]oct-6-yloxy)-3,5,8,10,12,14-hexamethyl-15-oxo-1-oxa-6-aza-cyclopentadec-11-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester (477198-91-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran	100%

3-(1H-indol-6-yl)-N-methoxy-N-methyl-acrylamide + trimethylsulfoxonium iodide (1774-47-6) → 2-(1H-indol-6-yl)-cyclopropanecarboxylic acid methoxy-methyl-amide (468718-44-7)

Conditions	Yield
With ammonium chloride In tetrahydrofuran; water	100%

3-hydroxychalcone (81226-95-1) + trimethylsulfoxonium iodide (1774-47-6)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water; dimethyl sulfoxide	100%

1-(4-chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane + trimethylsulfoxonium iodide (1774-47-6) → 2-(4-chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-oxirane (129578-71-8)

Conditions	Yield
In dimethyl sulfoxide	100%
In dimethyl sulfoxide; ethyl acetate

methyl 13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate (945686-05-5) + trimethylsulfoxonium iodide (1774-47-6) → methyl 8-cyclohexyl-5-((isopropylsulfonyl)carbamoyl)-11-methoxy-1,12b-dihydrocyclopropa[d]indolo[2,1-a][2]benzazepine-1a(2H)-carboxylate (1058166-17-8)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 0.75h; Stage #2: methyl 13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate In dimethyl sulfoxide for 1h;	100%
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 0.75h; Stage #2: methyl 13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate In dimethyl sulfoxide for 1h;	100%
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 0.75h; Stage #2: methyl 13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate In dimethyl sulfoxide for 1h;	100%
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 0.75h; Stage #2: methyl 13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate In dimethyl sulfoxide for 1h; Stage #3: With hydrogenchloride In water; dimethyl sulfoxide	100%
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide for 0.75h; Stage #2: methyl 13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate In dimethyl sulfoxide for 1h;	100%

2-{4-[4-[4-(2-methyl-5-chlorophenyl)piperazinyl]phenyl]-(2H,4H)-1,2,4-triazol-3-one-2-yl}-2(R/S)-methyl-2,4-difluoroacetophenone (359826-10-1) + trimethylsulfoxonium iodide (1774-47-6) → 2-[1-(R/S)-methyl-2-(2'-4'-difluorophenyl)-2,3-epoxypropyl]-4-{4-[4-(5-chloro-2-methylphenyl)piperazinyl]phenyl}-3-(2H,4H)-1,2,4-triazolone

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide at 15 - 30℃; for 1h; Stage #2: 2-{4-[4-[4-(2-methyl-5-chlorophenyl)piperazinyl]phenyl]-(2H,4H)-1,2,4-triazol-3-one-2-yl}-2(R/S)-methyl-2,4-difluoroacetophenone In dimethyl sulfoxide at 25 - 90℃; for 1h;	100%

furan-3-carboxaldehyde (498-60-2) + trimethylsulfoxonium iodide (1774-47-6) → 3-furyloxirane (158397-53-6)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With potassium hydroxide; water In acetonitrile at 40℃; for 0.5h; Stage #2: furan-3-carboxaldehyde In tetrahydrofuran at 40℃; for 18h;	100%

(trans)-N-methoxy-N-methyl-3-(2,3-dihydrobenzofuran-4-yl)propenamide (209256-81-5) + trimethylsulfoxonium iodide (1774-47-6) → (+/-)-(trans)-N-methoxy-N-rnethyl-2-(2,3-dihydrobenzofuran-4-yl)cyclopropanecarboxamide

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In DMF (N,N-dimethyl-formamide) for 0.166667h; Stage #2: (trans)-N-methoxy-N-methyl-3-(2,3-dihydrobenzofuran-4-yl)propenamide In DMF (N,N-dimethyl-formamide) at 20 - 40℃; for 3h;	100%

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) + trimethylsulfoxonium iodide (1774-47-6) → 3-((S)-2-tert-butoxycarbonylamino-6-dimethylsulfoxonium-5-oxo-hexanoylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (1253856-39-1)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In dimethyl sulfoxide Inert atmosphere; Stage #2: tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate In dimethyl sulfoxide at 20℃;	100%
With potassium carbonate In dimethyl sulfoxide at 50℃; for 21h; Temperature;	93%

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1) + trimethylsulfoxonium iodide (1774-47-6) → (S)-tert-butyl 2-(benzyloxycarbonylamino)-5-oxo-6-dimethylsulfoxonium hexanoate

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 5℃; for 1.33333h; Inert atmosphere;	100%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: tert-butyl N-benzyloxycarbonyl-L-pyroglutamate In N,N-dimethyl-formamide at 5℃; for 1.33h; Inert atmosphere;	100%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: tert-butyl N-benzyloxycarbonyl-L-pyroglutamate In N,N-dimethyl-formamide at 5℃; for 1.33333h;	100%

(7aSR,11aSR)-9-oxo-11a-(2,2,2-trifluoro-ethyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide + trimethylsulfoxonium iodide (1774-47-6) → C25H27F3N2O2

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: (7aSR,11aSR)-9-oxo-11a-(2,2,2-trifluoro-ethyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 20℃; for 18h;	100%

trimethylsulfoxonium iodide (1774-47-6) + benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5) → benzyl (2S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ6-sulfanylidene)-5-oxohexanoate

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran; dimethyl sulfoxide at -10℃;	100%
With potassium carbonate In dimethyl sulfoxide at 50℃; for 23h; Temperature; Reagent/catalyst; Solvent;	96%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 20℃; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran; dimethyl sulfoxide at -12℃;
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate; dimethyl sulfoxide In tetrahydrofuran at 25℃; for 1h; Large scale; Industrial scale; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran at -12℃; Large scale; Industrial scale;
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 25℃; for 2h; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran; dimethyl sulfoxide at 0 - 10℃; for 8h;

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-formyl-4,4-a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide + trimethylsulfoxonium iodide (1774-47-6) → N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(oxiran-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide (1616505-12-4)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil for 0.5h; Cooling with ice; Stage #2: N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-formyl-4,4-a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide In dimethyl sulfoxide; mineral oil at 20℃; for 2h; Cooling with ice;	100%

(E)-3-(2-fluoro-6-methoxyphenyl)-N-methoxy-N-methylacrylamide + trimethylsulfoxonium iodide (1774-47-6) → trans-2-(2-fluoro-6-methoxyphenyl)-N-methoxy-N-methylcyclopropanecarboxamide

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 35℃; for 1.5h; Stage #2: (E)-3-(2-fluoro-6-methoxyphenyl)-N-methoxy-N-methylacrylamide In dimethyl sulfoxide; mineral oil at 20 - 35℃; for 1.5h;	100%

trimethylsulfoxonium iodide (1774-47-6) + 2-((benzyloxy)methyl)-2-methyloxirane (97389-48-5) → (±)-1-(benzyloxy)-2-methylpent-4-en-2-ol

Conditions	Yield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); potassium tert-butylate In tert-butyl alcohol Inert atmosphere;	100%

Benzyloxymethyl-oxiran (2930-05-4) + trimethylsulfoxonium iodide (1774-47-6) → 1-(benzyloxy)-4-penten-2-ol (58931-16-1)

Conditions	Yield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); potassium tert-butylate In tert-butyl alcohol Reagent/catalyst; Inert atmosphere;	100%

trimethylsulfoxonium iodide (1774-47-6) + (2-benzyloxy-benzyl)-oxirane (62826-36-2) → 2-(2-(benzyloxy)benzyl)oxetane

Conditions	Yield
With iron(III) chloride; potassium tert-butylate In tert-butyl alcohol Inert atmosphere;	100%

2,4,4-trimethyl-cyclohexanone (2230-70-8) + trimethylsulfoxonium iodide (1774-47-6) → 4,6,6-trimethyl-1-oxaspiro[2.5]octane

Conditions	Yield
With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 24h; Corey-Tschaikosky Epoxidation;	100%

C17H17NO6 + trimethylsulfoxonium iodide (1774-47-6) → C14H20O4S

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran for 2h; Inert atmosphere; Darkness; Reflux; Stage #2: C17H17NO6 In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Darkness;	100%

1-methyl-2(1H)-quinoxalinone (6479-18-1) + trimethylsulfoxonium iodide (1774-47-6) → 1,3-dimethyl-1H-quinoxalin-2-one (3149-25-5)

Conditions	Yield
With potassium hydroxide In water at 100℃; for 2h; Sealed tube;	100%

trimethylsulfoxonium iodide (1774-47-6) + 1-(4-ethoxyphenyl)quinoxalin-2(1H)-one → 1-(4-ethoxyphenyl)-3-methylquinoxalin-2(1H)-one

Conditions	Yield
With potassium hydroxide In water at 100℃; for 2h; Sealed tube;	100%

trimethylsulfoxonium iodide (1774-47-6) + 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one (132563-81-6) → (2R,3S)-3-(2',4'-difluorophenyl)-3,4-epoxy-2-butyl-[3,4,5,6-tetrahydro-2H-pyran-2-yl]ether

Conditions	Yield
With (1S,2R,5S)-(+)-menthol; triphenylphosphine; lithium hydroxide In tetrahydrofuran at -20℃; for 20h; Inert atmosphere;	99.8%

(4-bromophenyl)(phenyl)methanone (90-90-4) + trimethylsulfoxonium iodide (1774-47-6) → 2-(4-bromophenyl)-2-phenyloxirane (1070671-69-0)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In tetrahydrofuran at 55℃; Inert atmosphere; Stage #2: (4-bromophenyl)(phenyl)methanone In tetrahydrofuran at 55℃; for 16h; Inert atmosphere;	99%
With sodium hydride 1.) THF, 55 deg C, 6 h, 2.) 55 deg C, 16 h; Yield given. Multistep reaction;

trimethylsulfoxonium iodide (1774-47-6) + hexyl-methyl-ketone (111-13-7) → 2-hexyl-2-methyloxirane (6924-86-3)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: hexyl-methyl-ketone In dimethyl sulfoxide; mineral oil at 20℃; for 5h; Sealed tube; Inert atmosphere;	99%
With potassium tert-butylate In dimethyl sulfoxide for 16h; Ambient temperature;	98%
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 16h; Corey-Chaykovsky reaction;	90%

trimethylsulfoxonium iodide (1774-47-6) + 2,2-Difluoro-2-(methylthio)-1-[4-(trifluoromethyl)phenyl]-1-ethanone (192862-15-0) → 2-[difluoro(methylthio)methyl]-2-[4-(trifluoromethyl)phenyl]oxirane (192862-20-7)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 2,2-Difluoro-2-(methylthio)-1-[4-(trifluoromethyl)phenyl]-1-ethanone In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 1h;	99%

Upstream product

• 67-68-5 dimethyl sulfoxide 
• 74-88-4 methyl iodide 
• 108-24-7 acetic anhydride 
• 61272-23-9 3-O-(β-D-galactopyranosyl)-D-arabinose 

Downstream Products

• 939-88-8 rac-(1R,2R)-2-phenylcyclopropanecarboxamide 
• 20963-46-6 Oxim d. Dimeren v. 2-Methylen-cyclohexanon 
• 24037-89-6 O-(2-Hydroxyimino-cyclohexyl)-2-methylen-cyclohexanonoxim 
• 60239-08-9 4-phenyl-4,5-dihydro-isoxazole 2-oxide 
• 15732-78-2 trans-2-Benzoyl-1-methyl-cyclopropan-⁽¹⁾-methylester 
• 7108-64-7 Dimethyl-oxo-sulfonium 
• 17886-29-2 1-Benzoyl-3-vinyltriazen-⁽²⁾ 
• 17886-30-5 Phenacyl-dimethyl-oxosulfoniumiodid 
• 22282-01-5 12-benzyl-5-methyl-5,6,7,8,10,11-hexahydro-spiro[6,10-epiazano-cycloocta[b]indole-9,2'-oxirane] 
• 19867-34-6 N-benzyl-1-oxa-6-azaspiro[2,5]-octane 
• 17322-97-3 1,2-epoxyundecane 
• 14296-80-1 1,2-dimethylenecyclobutane 
• 2855-19-8 Decyl-oxiran 
• 31002-34-3 1-Cyano-2,2-diphenylcyclopropane-1-carboxylic acid 

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Stereoselective Cyclopropanation of (-)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides

The synthesis of tri- and tetrasubstituted cyclopropanes from 3-aryl-substituted levoglucosenones (LGO) has been developed. In contrast to the unstabilised ylide dimethylsulfonium methylide which gives epoxides from LGO via 1,2-addition, we have found that the soft nucleophile dimethylsulfoxonium methylide affords cyclopropanes in moderate yields from LGO and in excellent yields and stereoselectivity with 3-aryl LGO derivatives. The use of 1,1,3,3-tetramethylguanidine as base in DMSO to generate the ylide provided the best yields and shortest reaction times. Ester stabilised sulfonium ylides could also be used to generate tetrasubstituted cyclopropane derivatives. One of the products was converted into a cyclopropyl lactone via Baeyer-Villiger oxidation to demonstrate the utility of applying cyclopropanation chemistry to LGO. Georg Thieme Verlag Stuttgart.New York.

Preparation method of medetomidine and intermediate thereof

The invention relates to a preparation method of 2-(2, 3-xylyl)-2-methyloxirane. The method is characterized in that the preparation process includes the following reaction shown as the specification, wherein Y is selected from Cl, Br, I, CH3SO4 or HSO4; alkali is selected from KOH, NaOH, LiOH, CsOH, K2CO3, Li2CO3, Cs2CO3, Na2CO3, EtONa, EtOK, (CH3)2CHONa, (CH3)2CHOK, (CH3)3CONa, (CH3)3COK, NH2Na or NH2K. The invention adopts the synthesis method using the 2-(2, 3-xylyl)-2-methyloxirane critical intermediate to prepare medetomidine.

1-[(4-hydroxypiperidin-4-yl)methyl]pyridin-2(1H)-one derivatives, preparation methods and uses thereof

Provided are N-[(4-hydroxypiperidin-4-yl)methyl]pyridin-2(1H)-one derivatives represented by formula I, stereoisomers, pharmaceutically acceptable salts or solvates thereof. The above compounds have the dual activities of 5-hydroxytryptamine 1A receptor ligand and selective serotonin reuptake inhibitor. The preparation methods of the above compounds, the uses of these compounds for the prevention or treatment of nervous system diseases related to 5-hydroxytryptamine system dysfunction and the pharmaceutical compositions containing these compounds are also provided.