Triphenylphosphine → Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

Participants

Reaction Conditions

Reaction Steps

4-(Chloromethyl)benzyl alcohol (4.68 g), methyl 3-(4-hydroxyphenyl)propanoate (5.40 g) and triphenylphosphine (9.20 g) were dissolved in a mixed solvent of toluene-tetrahydrofuran (60-30 mL) and cooled to 0° C., and diethyl azodicarboxylate (40% toluene solution, 15.2 g) was added dropwise with vigorously stirring. After the completion of the dropwise addition, the temperature of the reaction mixture was allowed to return to room temperature and the mixture was further stirred for 1 hr. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:19 to 1:1 by volume ratio) to give the title compound (5.19 g, yield 54%) as colorless crystals.

Provenance & Evidence