Acetic Acid → HCID 22845931, compound

Participants

Reaction Steps

To 40 g (1 mole) of 60% sodium hydride washed with dry pentane was added 300 ml of dry tetrahydrofuran, and a solution of 176 g (1.1 moles) of diethyl malonate in 350 ml of tetrahydrofuran was slowly added into the obtained suspension with stirring. After the dropwise addition, 20.7 g (0.1 mole) of (S)-4-bromo-1,2-butanediol acetonide was added into the mixture over a period of 2 hours. The mixture was stirred for 20 hours to effect reaction. Then acetic acid dissolved in ether was added to the mixture to neutralize the excessive alkali, ether was added to the mixture, and the mixture was washed with a saturated saline solution and dried over magnesium sulfate. The solvent was removed under a reduced pressure, and optical resolution was carried out by the silica gel column chromatography to obtain 5.5 g of (2S,5S)-2-carboxy-5-hydroxymethyl-δ-valerolactone.

Provenance & Evidence