Boron trifluoride etherate → HCID 15754137, compound

Participants

Reaction Conditions

Reaction Steps

A benzene solution of 23.6 g (0.1 mol) of 3,5-dichloro-4-methoxy-α,α-dimethylbenzyl alcohol and 13.9 g (0.12 mol) of trimethylsilyl azide were cooled with ice water, and 17.1 g (0.12 mol) of boron trifluoride ethyl etherate was dropwise added thereto at a temperature not higher than 20° C. under stirring. After completion of the dropwise addition, the mixture was stirred for one hour as it was and further at room temperature for 4 hours. The reaction solution was poured into ice water, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with water. To this benzene solution, 5.1 g (0.01 mol) of n-hexadecyl tri-n-butylphosphonium bromide was added, and an aqueous solution of 32.4 g (0.9 mol) of sodium borohydride was dropwise added thereto at 80° C. in three times. The reaction solution was poured into water. The organic layer was washed with water and then subjected to liquid separation by an addition of concentrated hydrochloric acid. The aqueous layer was alkalified with sodium hydroxide and then extracted with diethyl ether. The ether solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 14.9 g of the desired compound.

Provenance & Evidence