Benzyl Chloride → ethyl 3,4-dihydro-6-(phenylmethoxy)-2H-1-benzopyran-2-carboxylate

Participants

Reaction Steps

To a stirred solution of 5.6 parts of ethyl 3,4-dihydro-6-hydroxy-2H-1-benzopyran-2-carboxylate in 90 parts of N,N-dimethylformamide were added portionwise 1.2 parts of a sodium hydride dispersion 50%. Upon completion, stirring was continued for 30 minutes. A solution of 3.1 parts of (chloromethyl)benzene in 18 parts of N,N-dimethylformamide was added dropwise. Upon completion, the whole was stirred for 22 hours at 70° C. The reaction mixture was evaporated. Water was added. The product was extracted with 1,1'-oxybisethane. The extract was washed with a sodium chloride solution 10%, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 6 parts (76.9%) of ethyl 3,4-dihydro-6-(phenylmethoxy)-2H-1-benzopyran-2-carboxylate as a residue (intermediate 29).

Provenance & Evidence