Water → HCID 57517505, compound

Temperature

0 °C

To a suspension of lithium aluminum hydride (1.13 g) in THF (100 mL) was slowly added a solution of ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}cyclohexanecarboxylate (12.2 g) in THF (100 mL) under ice-cooling. The reaction mixture was stirred at 0° C. for 1 hr, and water (1.2 mL) and 1M aqueous sodium hydroxide solution (1.2 mL) were successively added thereto. The mixture was stirred at room temperature for 30 min, and water (3.6 mL) was further added thereto. The mixture was stirred at room temperature for 1 hr, and the insoluble material was filtered off through celite under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (9.38 g).

1. temperaturecooling
2. stirringThe mixture was stirred at room temperature for 30 min
3. stirringThe mixture was stirred at room temperature for 1 hr
4. filtrationthe insoluble material was filtered off through celite under reduced pressure
5. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

ORD record

ord-ec22dd554b694e72af74d513ea672ab1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703758B2