Alpha-Methylstyrene → HCID 11052785, compound

Participants

Reaction Conditions

Reaction Steps

A solution of an (R)-binaphthol-dichlorotitanium complex which had been prepared in the same manner as in Example 1 was cooled to -30° C. and added with 118 mg (1 mmole) of α-methylstyrene and 88 mg (1 mmole) of methyl glyoxylate, followed by reaction for 15 hours. Then, 10 ml of an aqueous sodium hydrogen-carbonate solution was added to terminate the reaction. The reaction mixture was filtered through Celite and extracted with two 20 ml portions of diethyl ether and two 20 ml portions of ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. Thereafter, the solvents were distilled off, and hexane was added to the residue to crystallize binaphthol. The remaining solution was purified by means of silica gel column chromatography to obtain 200 mg of methyl (R)-2-hydroxy-4-phenyl-4-pentenoate. The yield was 97%.

Provenance & Evidence