Dichloromethane → HCID 67895218, compound

Participants

Reaction Steps

A mixture of (S)-(+)-methyl-3-hydroxy-2-methylpropionate (10.0 g), 2,3-dihydropyran (10.0 g) and D,L-10-camphorsulfonic acid in CH2Cl2 (200 ml) was stirred for 30 min at room temperature. The reaction was quenched by the addition of saturated aqueous NaHCO3, followed by extraction with ether. The combined extracts were washed with water, dried over MgSO4 and concentrated to give 17.1 g of crude product. A solution of crude product (17.1 g) in ether (30 ml) was added dropwise during 40 min to a stirred and ice cooled suspension of LiAlH4 (3.21 g) in dry ether (300 ml). The stirring was continued for 30 min at room temperature. The excess LiAlH4 was decomposed by the successive addition of water (8 ml), 15% NaOH (8 ml) and water (24 ml) and the stirred and ice-cooled mixture was filtered. The filtrate was dried over MgSO4 and concentrated in vacuo. The residue was distilled to give 14.6 g of (1). b.p. 85 89/3.5 mmHg.

Provenance & Evidence