Diethyl Ether → HCID 57137252, compound

Participants

Reaction Steps

After completion of the dropwise addition, the mixture was stirred for 15 minutes to synthesize a lithium enolate of t-butyl acetate. The reaction mixture was cooled to -50° C. in dry ice-acetone, and a solution of 3.3 g (16.5 mmole) of methyl (3S)-4-t-butoxy-3-hydroxybutanoate as prepared in Example 1 in 15 ml of tetrahydrofuran was added to the mixture through the dropping funnel over 20 minutes, followed by stirred for an additional 1.5 hours. After confirming the completion of the reaction by gas chromatography, 30 ml of a saturated aqueous solution of ammonium chloride and 100 ml of diethyl ether were added to the reaction mixture to conduct extraction. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (diethyl ether/hexane: 1/1 by volume) to obtain 2.3 g (yield: 46%) of t-butyl (5S)-6-t-butoxy-5-hydroxy-3-oxohexanoate.

Provenance & Evidence