Thioglycerol → Diethyl 5-(hydroxymethyl)-1,3-oxathiolane-2,2-dipropanoate

HRID 1383154Notes

Reaction equation

HRID 1383154 reaction equation
[SH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].O=[C:8]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].B(F)(F)F.CCOCC>C(Cl)Cl>[OH:5][CH2:4][CH:3]1[O:6][C:8]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:1][CH2:2]1

Participants

5

Reactant 3

HCID 7291ThioglycerolHCID 8000Boron trifluoride etherateHCID 80592Diethyl 4-oxoheptanedioate

Product 1

HCID 14405958Diethyl 5-(hydroxymethyl)-1,3-oxathiolane-2,2-dipropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure of Example 1 using 3-mercapto-1,2-propanediol (10.8 g, 0.1 mol), diethyl 4-oxopimelate (23 g, 0.1 mol) and boron trifluoride etherate (2.5 ml) in methylene chloride (300 ml). The crude product was chromatographed on silica gel using 40% ethyl acetate/hexane as eluent to give 14.5 g (45%) of product.

Workup

  1. customThe crude product was chromatographed on silica gel using 40% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-a4509da389a147c48e0c3ae9598e465b
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

Loading…