Acetone → Methyl 2-[[4-[2-(benzyloxymethoxy)ethyl]phenyl]amino]-2-methylpropionate

Participants

Reaction Steps

To a stirred solution of 4-[2-(benzyloxymethoxy)ethyl]aniline (1.4 g) and 1,1,1-trichloro-2-methyl-2-propanol hydrate (2.0 g) in acetone (10 ml) was added potassium hydroxide (2.9 g) three times (total 8.7 g) at intervals of 10 minutes under ice-cooling, and the mixture was stirred for 21 hours at room temperature. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ice-water and washed with diethyl ether. The aqueous layer was neutralized with 2N hydrochloric acid, and the solvent was removed under reduced pressure. The residue was dissolved in a mixed solvent of dichloromethane (10 ml) and methanol (5.0 ml), a solution of diazomethane in diethyl ether was added until the reaction solution was colored, and the mixture was stirred for 3 hours at room temperature. After the reaction mixture was concentrated under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent:hexane/ethyl acetate=1/1) gave methyl 2-[[4-[2-(benzyloxymethoxy)ethyl]phenyl]amino]-2-methylpropionate (888 mg).

Provenance & Evidence