Imidazole → HCID 58018637, compound

To a solution of ethyl 4-hydroxycyclohexane carboxylate (5 g, 29.03 mmol) in dichloromethane (200 mL) was added imidazole (4.97 g, 73 mmol) and tert-butylchlorodiphenylsilane (15.96 g, 15.2 mL, 58 mmol). The reaction mixture was allowed to stir at room temperature over night. The reaction mixture was poured into water (125 mL) in a separatory funnel and the phases were separated. The aqueous phase was extracted with dichloromethane (2×200 mL). The combined organic solutions were washed with brine, dried over Na2SO4, and concentrated under vacuum. Purification by column chromatography on silica gel eluting with ethyl acetate in heptanes (0-10%) afforded 10.55 g (89%) of the title compound.

1. customthe phases were separated
2. extractionThe aqueous phase was extracted with dichloromethane (2×200 mL)
3. washThe combined organic solutions were washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under vacuum
6. customPurification by column chromatography on silica gel eluting with ethyl acetate in heptanes (0-10%)

ORD record

ord-8fb9f724b97041e9b185b50a728be56c

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735385B2