Reaction #69607

Reaction equation

9

2-Methoxy-N-[(1E)-phenylmethylene]aniline

BnMgCl

water

→

B3

Yield 96.1%

N-(1,2-Diphenylethyl)-2-methoxyaniline

Yield 96.1%

Solvents

THF

THF

Conditions

Workup

1. 1
   TemperatureThis mixture was slowly warmed to room temperature
2. 2
   OtherThe resulting mixture was evaporated to dryness
3. 3
   OtherThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.)

Procedure

To a solution of 4.22 g (20.0 mmol) of 9 in 50 mL of THF, 48.0 mL (26.0 mmol) of 0.55 M BnMgCl in THF was added with vigorous stirring at −80° C. This mixture was slowly warmed to room temperature, and then 2 mL of water was added. The resulting mixture was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.) to give 5.83 g (96%) of B3.

Source