Sodium Hydroxide → HCID 22664978, compound

Temperature

-10 °C

Lithium aluminum hydride (0.64 g, 16.8 mmol) was mixed with ether (20 ml) and cooled to −10° C. Thereto was added dropwise a solution of ethyl 1-(1-hydroxy(2-chlorophenyl)methyl)cyclopentanecarboxylate (3.1 g, 11.2 mmol) in ether (5 ml) at the same temperature over 15 min, and the mixture was stirred at −10° C. for 1 h, and at room temperature for 3 h. The mixture was cooled to −20° C. and 10%—NaHCO3 aq. (2 ml) was added dropwise, then 20%—NaOH aq. (2 ml) was added dropwise. The mixture was stirred for 30 min and sludge was removed by decantation. The organic layer was washed with water (50 ml), dried over anhydrous sodium sulfate, concentrated to dryness, and purified by silica gel column chromatography (hexane:ethyl acetate =2:1) to give the title compound 2.2 g (quant.) as a colorless oil.

1. waitat room temperature for 3 h
2. temperatureThe mixture was cooled to −20° C.
3. stirringThe mixture was stirred for 30 min
4. customsludge was removed by decantation
5. washThe organic layer was washed with water (50 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated to dryness
8. custompurified by silica gel column chromatography (hexane:ethyl acetate =2:1)

ORD record

ord-60c586747090455ab1ff68e46eef07d6

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800778B1