Ammonium Chloride → HCID 19966000, compound

A solution of 1.01 g (6.73 mmol) of 2-benzyloxyacetaldehyde in 6 ml of diethyl ether was added dropwise over a period of 3 minutes to 14 ml (8.6 mmol) of a 0.6M diethyl ether solution of 3-cyclohexylpropylmagnesium bromide, whilst ice-cooling, and the resulting mixture was stirred for 30 minutes at the same temperature and then for 10 minutes at room temperature. In order to stop the reaction, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. The reaction mixture was then diluted with diethyl ether, and the diluted mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 150 g of silica gel, using a 1:3 by volume mixture of ethyl acetate and hexane as the eluent, to give 1.27 g (yield 68%) of the title alcohol derivative as an oil.

1. temperaturecooling
2. waitfor 10 minutes at room temperature
3. customthe reaction
4. washthe diluted mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order
5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
6. customthe solvent was removed by distillation under reduced pressure
7. customThe resulting residue was purified by column chromatography through 150 g of silica gel
8. additionby volume mixture of ethyl acetate and hexane as the eluent

ORD record

ord-196f279f182842eaae81b5d406e298d6

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05614550