Réaction #1269883

Équation de réaction

NaOH

LiAlH4

ethyl 2,6-dimethyl-4-phenylnicotinate

water

Water

→

(2,6-dimethyl-4-phenylpyridin-3-yl)methanol

Rendement 102.4%

Solvants

EtOAc

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITthe stirring was continued for 75 min
2. 2
   Autrethe solvent was removed in vacuo

Mode opératoire

LiAlH4 (1 M solution in THF, 8.93 mL, 8.93 mmol) was added dropwise to a solution of ethyl 2,6-dimethyl-4-phenylnicotinate (940 mg, 3.57 mmol) in THF (38 mL) at 0° C. After stirring for 45 min, the reaction mixture was allowed to warm to room temperature and the stirring was continued for 75 min Water (0.2 mL) was added at 0° C. followed by NaOH (2 M, 0.2 mL) and water (0.2 mL). After the addition of excess EtOAc and filtration, the solvent was removed in vacuo providing (2,6-dimethyl-4-phenylpyridin-3-yl)methanol as a pale yellow gum (780 mg, >99%). ESI-MS [M+H]+=214.1.

Source