Ammonium Chloride → HCID 22662121, compound

Participants

Reaction Conditions

Reaction Steps

1.3 ml of methyllithium (2.1 mmol, 1.6 M in diethyl ether) are introduced into 1 ml of diethyl ether and, at −78° C., 600 mg (1.99 mmol) of tert-butyl 4-bromo-3,5-dimethylphenylcarbamate (Example IV) in 2 ml of diethyl ether/1 ml of THF are added. After 20 min, 1.53 ml of t-BuLi (2.6 mmol, 1.7 M in pentane) are added dropwise and the mixture is stirred at −78° C. for 30 min. 3-(4-Fluorobenzyl)-4-methoxybenzaldehyde dissolved in 3 ml of THF is added dropwise. After stirring at −78° C. for 1 h, aqueous NH4Cl solution is added. The mixture is diluted with diethyl ether and extracted with water, and the organic phase is dried and concentrated in a rotary evaporator. Chromatography (cyclohexane/ethyl acetate=6:1) affords 493 mg (46%) of tert-butyl 4-[[3-(4-fluorobenzyl)-4-methoxyphenyl](hydroxy)methyl]-3,5-dimethylphenylcarbamate.

Provenance & Evidence