Methanol → 2-Methoxy-3-(phenylmethoxy)benzeneacetonitrile

Participants

Reaction Conditions

Reaction Steps

9.3 g (83 mmol) Potassium tert-butoxide in 30 mL 1,2-dimethoxyethane are cooled to −30° C. 9.1 g (45 mmol) toluene-4-sulfonylmethylisocyanide in 30 mL 1,2-dimethoxyethan are added slowly and the resulting mixture is cooled to −50° C. A mixture of 10.0 g (41.3 mmol) 3-benzyloxy-2-methoxy-benzaldehyde (see CN 102451178) in 80 mL 1,2-dimethoxyethane are added within 30 min and stirred for 2 h at −50° C. After that time 60 mL MeOH are added and stirred for 2 h under reflux. The mixture is cooled to r.t., diluted with water and extracted with DCM. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel; cyclohexane/EtOAc 4:1) to yield the desired product.

Provenance & Evidence