Ethyl Acetate → HCID 69143601, compound

Participants

Reaction Conditions

Reaction Steps

Zinc chloride (1.0 M diethyl ether solution; 8.8 ml, 8.8 mmol) was added to tetrahydrofuran (5 ml), and sodium borohydride (605.3 mg, 16.0 mmol) was added thereto with stirring at 0° C. The mixture was irradiated with ultrasonic waves for 10 minutes using a commercially available ultrasonic cleaner. The mixture was taken out of the ultrasonic cleaner and cooled to −5° C., and a solution of allyl 5-[(4-methoxybenzyl)oxy]-2,5-dioxopentanoate (1.84 g, 6.0 mmol) obtained from Example 2-(1) in tetrahydrofuran (5 ml) was added thereto over a period of 10 minutes. The resulting mixture was stirred for 30 minutes, and then a saturated aqueous solution of ammonium chloride was added thereto to stop the reaction followed by extraction of the product with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to afford an oily residue. The residue was subjected to chromatography on a silica gel (65 g) column (eluent; ethyl acetate:hexane=3:10˜2:5) to afford the title compound (1.26 g, 68% yield) as a colorless oil.

Provenance & Evidence