Toluene → 3-Ethyl-5-methyl-4-oxiranylmethoxy-benzonitrile

Participants

Reaction Steps

To a solution of 3-ethyl-4-hydroxy-5-methyl-benzonitrile (5.06 g, 31.4 mmol) in THF (80 mL), PPh3 (9.06 g, 34.5 mmol) and (R)-glycidol (2.29 mL, 34.5 mmol) were added. The mixture was cooled to 0° C. before DEAD in toluene (15.8 mL, 34.5 mmol) was added. The mixture was stirred for 18 h while warming up to rt. The solvent was evaporated and the crude product was purified by CC eluting with Hept:EA 7:3 to give 3-ethyl-5-methyl-4-oxiranylmethoxy-benzonitrile as a yellow oil (5.85 g). LC-MS: tR=0.96 min; [M+42]+=259.08.

Provenance & Evidence