Reaction #1780

Reaction equation

5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-one

NaBH4

→

5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-ol

Solvents

MeOH

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Otherthe crude oil that was chromatographed on a silica gel column
3. 3
   Washhexanes and eluted with same
4. 4
   Otherthe solvent was removed under reduced pressure

Procedure

A stirred solution of 5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-one (240 mg, 1.3 mmol) in MeOH (6.5 mL) was cooled to 0° C. under Argon and treated with NaBH4 (48 mg, 1.3 mmol). The reaction was stirred over 14 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil that was chromatographed on a silica gel column packed in 95:5 EtOAc:hexanes and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure to give 5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-ol.

Source