tert-Butyldimethylsilyl chloride → HCID 86677879, compound

HRID 1499959Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:18])=[C:4]([CH:14]([OH:17])[CH2:15][OH:16])[C:5]([O:11][CH2:12][CH3:13])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>ClCCCl>[Si:28]([O:16][CH2:15][CH:14]([C:4]1[C:5]([O:11][CH2:12][CH3:13])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[F:18])[OH:17])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

1-[5-Chloro-3-(1,2-dihydroxyethyl)-2-ethoxy-4-fluorophenyl]ethanone (700 mg, 2 mmol) (from Step 2, peak 2) was stirred in 1,2-dichloroethane (6 mL) with N,N-diisopropylethylamine (4.0 mL, 23 mmol) and a 1.0 M solution of tert-butyldimethylsilyl chloride in 1,2-dichloroethane (7.6 mL) was added. The mixture was heated to 80° C. for 3 hours and cooled to rt. Evaporation and purification on silica gel using ethyl acetate in hexanes (0-50%) gave the desired compound 800 mg, 80%. LCMS calculated for C18H28ClFO4SiNa (M+Na)+: m/z=413.1; found: 413.1.

Workup

temperaturecooled to rt
customEvaporation and purification on silica gel

Sources & evidence

ORD record: ord-7f69611a8a6847eaaad600305bde2f8f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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