Chlorotrimethylsilane → 1-Trimethylsilyloxy-1-tert-butylthio-2,2-difluoroethene

HRID 22504Notes

Reaction equation

[F:1][CH:2]([F:10])[C:3]([O:5]C(C)(C)C)=[S:4].[CH3:11][Si:12]([CH3:15])([CH3:14])Cl.C([N-][CH:20]([CH3:22])[CH3:21])(C)C.[Li+].O1CCC[CH2:25]1>>[CH3:11][Si:12]([CH3:15])([CH3:14])[O:5][C:3]([S:4][C:20]([CH3:22])([CH3:25])[CH3:21])=[C:2]([F:1])[F:10]

Participants

Reactant 4

HCID 6397Chlorotrimethylsilane

HCID 8028Tetrahydrofuran

HCID 2724682Lithium diisopropylamide

HCID 53863274tert-Butyl difluorothioacetate

Product 1

HCID 106101031-Trimethylsilyloxy-1-tert-butylthio-2,2-difluoroetheneYield 65%

Conditions

Temperature: -78 °C

Procedure

tert-Butyl difluorothioacetate (100 mg) was dissolved in tetrahydrofuran (5 ml) and the solution was cooled to -78° C. Trimethylchlorosilane (151 μl) and lithium diisopropyl amide (327 μl, 2 M solution in heptane/tetrahydrofuran/ethyl-benzene). The solution was stirred for 1 hour at -78° C. then warmed to 25° C. The above product formed in a 65 percent yield as determined by 19F NMR Spectroscopy. 19F NMR (C6D6 vs C6F6, ppm) -104.2 (d, J=28 Hz), -92.6 (d, J=28 Hz).

Workup

temperaturethen warmed to 25° C
customThe above product formed in a 65 percent yield

Sources & evidence

ORD record: ord-181376df548944db8a601571b3bfc753
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05428176

Reaction notes

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