Dimethyl Sulfoxide → HCID 10492826, compound

HRID 634967Notes

Reaction equation

[H-].[Na+].[CH3:3]S(C)=O.[I-].C[S+](C)(C)=O.[CH:13]1([S:16][C:17]([F:29])([F:28])[C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])=[O:19])[CH2:15][CH2:14]1>O1CCCC1>[CH:13]1([S:16][C:17]([F:29])([F:28])[C:18]2([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[CH2:3][O:19]2)[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 60% sodium hydride (1.0 g, 0.025 mol) in tetrahydrofuran (50 ml)—dimethylsulfoxide (70 ml) was heated to an external temperature of 50° C., followed by the addition of trimethylsulfoxonium iodide (5.6 g, 0.025 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-cyclopropylthio-2,2,2′,4′-tetrafluoroacetophenone (5.6 g, 0.021 mol) in tetrahydrofuran (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-[(cyclopropylthio)(difluoro)methyl]-2-(2,4-difluorophenyl)oxirane (5.0 g, yield: 86%) 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-0300c455515241a4bed1d93f9d9c409e
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184396B2

Reaction notes

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