Dichloromethane → HCID 67895218, compound

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.

1. customThe reaction was quenched by the addition of saturated aqueous NaHCO3
2. extractionfollowed by extraction with ether
3. washThe combined extracts were washed with water
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customto give 17.1 g of crude product
7. stirringa stirred
8. temperatureice cooled
9. waitThe stirring was continued for 30 min at room temperature
10. stirringthe stirred
11. temperatureice-cooled mixture
12. filtrationwas filtered
13. dry with materialThe filtrate was dried over MgSO4
14. concentrationconcentrated in vacuo
15. distillationThe residue was distilled

ORD record

ord-0e959aaa0d6f43ca91bc276689c4f40f

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05081152