Dimethyl Sulfoxide → HCID 10825624, compound

HRID 2287442Notes

Reaction equation

[H-].[Na+].[CH3:3]S(C)=O.[I-].C[S+](C)(C)=O.[CH2:13]([S:15][C:16]([F:28])([F:27])[C:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26])=[O:18])[CH3:14]>C1COCC1>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:17]1([C:16]([S:15][CH2:13][CH3:14])([F:27])[F:28])[CH2:3][O:18]1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 60% NaH (876 mg, 0.022 mol) in THF (30 ml) - DMSO (50 ml) was heated to an external temperature of 50° C., followed by the addition of trimethylsulfoxonium iodide (4.8 g, 0.022 mol) in portions. After stirring at the same temperature for one hour, the reaction mixture was cooled to -20° C. and added dropwise with a solution of 2-ethylthio-2,2,2', 4'-tetrafluoroacetophenone (4.6 g, 0.018 mol) in THF (20 ml). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into ice water, followed by extraction with ethyl acetate. The extract was washed successively with water and saturated saline and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure, whereby 2-(2,4-difluorophenyl)-2-[(ethylthio) (difluoro)methyl]oxirane (4.3 g, yield: 90.0%) was obtained as a pale yellow oil.

Workup

temperaturethe reaction mixture was cooled to -20° C.
stirringThe resulting mixture was stirred at room temperature for 2 hours
extractionfollowed by extraction with ethyl acetate
washThe extract was washed successively with water and saturated saline
dry with materialdried over magnesium sulfate
distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record: ord-83c168a6d4ca40499a889bb73c187c48
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06083968

Reaction notes

Loading…