Sodium Hydroxide → HCID 13676044, compound

Temperature

-10 °C

Lithium aluminum hydride (0.39 g, 10.2 mmol) was mixed with ether (12 ml) and the mixture was cooled to −10° C. Thereto was added dropwise a solution of ethyl 1-[hydroxy(phenyl)methyl]cyclopropanecarboxylate (1.5 g, 6.8 mmol) in ether (3 ml) at the same temperature over 15 min, and the mixture was stirred at −10° C. for 1 h and at room temperature for 2 h. Thereafter, 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, and the mixture was stirred for 30 min. Sludge was removed by decantation and 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=3:1) to give the title compound (1.2 g, 98.9%) as a colorless oil.

1. temperatureThereafter, the mixture was cooled to −20° C.
2. stirringthe mixture was stirred for 30 min
3. customSludge was removed by decantation
4. washthe organic layer was washed with water (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated to dryness
7. custompurified by silica gel column chromatography (hexane:ethyl acetate=3:1)

ORD record

ord-a5cad511287540869437a3c89a647778

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800778B1