Reaction #4508

Reaction equation

water

Sodium borohydride

4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzonitrile

N,N-dimethylformamide

→

4-[2-hydroxy-2-(5-methyl-phenyl-4-oxazolyl)ethoxy]benzonitrile

Yield 92.7%

Solvents

methanol

Conditions

Workup

1. 1
   Otherthe crystals which separated out
2. 2
   Filtrationwere collected by filtration

Procedure

Sodium borohydride (0.654 mg) was added to a suspension of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]benzonitrile (5.5 g) in methanol (100 ml)-N,N-dimethylformamide (50 ml), followed by stirring at room temperature for 1 hour. The reaction solution was poured into water and the crystals which separated out were collected by filtration to give 4-[2-hydroxy-2-(5-methyl-phenyl-4-oxazolyl)ethoxy]benzonitrile (5.1 g, 92.7%). Recrystallization from acetone afforded colorless neddles, m.p. 176°-177° C.

Source