(Methoxymethyl)trimethylsilane → HCID 86713710, compound

Temperature

-25 °C

To a solution of (methoxymethyl)trimethylsilane (694 mg, 5.75 mmol) in tetrahydrofuran (6.8 mL) at −78° C. was added drop-wise sec-butyllithium (1.4 M, 4.45 mL, 6.23 mmol). The solution was warmed to −25° C., held at that temperature for 30 minutes, then cooled to −78° C. To the reaction was added drop-wise 3-(4-chlorophenyl)cyclohexanone (prepared according to the method of G. A. Whitlock et al., Bioorg. Med. Chem. Lett. 2009, 19, 3118-3121) (1.0 g, 4.8 mmol). The reaction was warmed to −25° C. and stirred for 30 minutes, then allowed to slowly warm to room temperature and stir for 48 hours. The reaction was diluted with tetrahydrofuran (10 mL), quenched with saturated aqueous ammonium chloride solution, and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to provide the crude title compound as a pale yellow oil. Yield: 1.25 g. This material was used directly in the following step. GCMS m/z 236 (M+).

1. temperaturecooled to −78° C
2. customprepared
3. temperatureThe reaction was warmed to −25° C.
4. temperatureto slowly warm to room temperature
5. stirringstir for 48 hours
6. customquenched with saturated aqueous ammonium chloride solution
7. extractionextracted three times with ethyl acetate
8. dry with materialThe combined organic layers were dried over magnesium sulfate
9. concentrationconcentrated in vacuo

ORD record

ord-9899519e612a487281f093b6643d850d

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916564B2