Chlorotrimethylsilane → HCID 14774099, compound

HRID 1081396Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[Li+].CC([N-]C(C)C)C.[F:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[C:30]1[O:31][CH2:32][C:33]([CH3:36])([CH3:35])[N:34]=1.Cl[Si:38]([CH3:41])([CH3:40])[CH3:39]>C1COCC1.O>[F:21][C:22]1[C:27]([Si:38]([CH3:41])([CH3:40])[CH3:39])=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[C:30]1[O:31][CH2:32][C:33]([CH3:36])([CH3:35])[N:34]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 8.7 mL (62.1 mmol) of diisopropylamine in 100 mL of dry THF under argon was cooled to -78° C. and treated with 28.3 mL (56.6 mmol) of 2.0M n-butyllithium. The LDA solution was stirred at -78° C. for 15 minutes. To this solution was added a solution of 11.8 g (51.5 mmol) of 2-(2,4,5-trifluorophenyl)-4,4-dimethyl-2-oxazoline in 50 mL of THF, and the reaction mixture was stirred for 1 hour at -78° C. To the reaction mixture was added 13 mL (102.5 mmol) of chlorotrimethylsilane, and the solution was warmed to room temperature. Water was added; the organic layer was dried over magnesium sulfate and concentrated. The crude product was chromatographed on silica gel (E. Merck 230-400 Mesh), eluting with 80:20 chloroform:ethyl acetate to give 12.9 g of the title compound, mp 71°-72° C.

Workup

temperaturethe solution was warmed to room temperature
dry with materialthe organic layer was dried over magnesium sulfate
concentrationconcentrated
customThe crude product was chromatographed on silica gel (E. Merck 230-400 Mesh)
washeluting with 80:20 chloroform

Sources & evidence

ORD record: ord-f5d89336c91343ce97d9c2e867313943
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585491

Reaction notes

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