Methyl iodide → Ethyl 4-[(tert-butyldimethylsilyl)oxy]-1-methylcyclohexanecarboxylate

Temperature

0 °C

Ethyl 4-(tert-butyldimethylsilyloxy)cyclohexanecarboxylate (3 g, 10.47 mmol) in THF (20 mL) was added to a freshly prepared solution of LDA (prepared from n-butyllithium (26.2 mmol) in hexane and diisopropylamine (3.73 mL, 26.2 mmol) in 7 mL of THF) at −78° C. the reaction was stirred for 1 h, warmed to 0° C. for 5 min, cooled again to −78° C. followed by addition of methyl iodide (2.292 mL, 36.7 mmol). The reaction mixture was allowed to warm to room temperature overnight, quenched with aqueous ammonium chloride, and concentrated under vacuum to remove volatile solvents. The residual aqueous mixture was extracted with ether, and the ether solution was dried and concentrated under vacuum to give the crude product as an oil which was further purified via normal phase chromatography on silica gel (Biotage SP1, 40+S column) to give product (2.7 g; MS: (M+H)+=301.3) as a clear oil.

1. temperaturecooled again to −78° C.
2. temperatureto warm to room temperature overnight
3. customquenched with aqueous ammonium chloride
4. concentrationconcentrated under vacuum
5. customto remove volatile solvents
6. extractionThe residual aqueous mixture was extracted with ether
7. dry with materialthe ether solution was dried
8. concentrationconcentrated under vacuum

ORD record

ord-9c0403d32330491cb4c1dd6737be48de

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697739B2