Methanol → {4-[2-(Dimethylamino)ethoxy]phenyl}methanol

Participants

Reaction Steps

To a stirred solution of the aldehyde 2c (5.9 g, 0.031 mol, 1.0 eq.) in methanol (20 mL) at 22° C. sodium borohydride (0.58 g, 0.015 mol, 0.5 eq.) is added in portions. The reaction is stirred for 30 min. TLC at this point shows no starting material, mostly product (EtOAc/hexane/triethylamine 5:5: 1). The reaction mixture is diluted with water (50 mL), extracted with methylene chloride (3×40 mL), and dried over MgSO4. The solution is concentrated on a rotary evaporator to give 5.25 g (88%) of the alcohol 3c as a thick oil.

Provenance & Evidence