Triethylsilane → HCID 67301354, compound

In a 100 mL flask with stir bar and 4-(2-methoxybenzoyl)cyclohexanecarboxylic acid methyl ester (900 mg; 3.26 mmol), trifluoroacetic acid (10 mL) was chilled to 0° C. and triethylsilane (2 g; 16.3 mmol) was added over 1 minute. Mixture was allowed to warm to room temperature. After 48 hours, mixture was concentrated in vacuo and reduced by half volume. The mixture was poured into a water (40 mL) solution and extracted with ethyl acetate (EtOAc) (4×10 mL). The combined organic layers were washed with NaHCO3 (40 mL), brine (40 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using EtOAc/hexane (gradient system), to obtain 4-(2-methoxybenzyl)cyclohexanecarboxylic acid methyl ester (0.78 g, 91% yield).

1. concentrationmixture was concentrated in vacuo
2. additionThe mixture was poured into a water (40 mL) solution
3. extractionextracted with ethyl acetate (EtOAc) (4×10 mL)
4. washThe combined organic layers were washed with NaHCO3 (40 mL), brine (40 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationThe organic layer was concentrated in vacuo
7. customto obtain the crude mixture, which
8. customwas purified by of silica gel flash chromatography

ORD record

ord-784647dfb97342cd95f46f8aaa747698

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985755B2