Dimercaprol → Methyl 4-(mercaptomethyl)-2-methyl-1,3-oxathiolane-2-butanoate

HRID 1650261Notes

Reaction equation

HRID 1650261 reaction equation
[SH:1][CH:2]([CH2:5][SH:6])[CH2:3][OH:4].[C:7]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=O)[CH3:8].B(F)(F)F.CCOCC>C(Cl)Cl>[SH:6][CH2:5][CH:2]1[CH2:3][O:4][C:7]([CH3:8])([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[S:1]1

Participants

5

Reactant 3

HCID 3080DimercaprolHCID 8000Boron trifluoride etherateHCID 84129Methyl 5-oxohexanoate

Product 1

HCID 14405957Methyl 4-(mercaptomethyl)-2-methyl-1,3-oxathiolane-2-butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure of Example 1 using 2,3-dimercaptopropanol (2.8 g, 0.022 mol), methyl 4-acetylbutyrate (3.2 g, 0.022 mol) and boron trifluoride etherate (0.62 ml) in methylene chloride (70 ml). The crude product was chromatographed on silica gel using 10% ethyl acetate/hexane as eluent to give 0.91 g (16.5%) of product.

Workup

  1. customThe crude product was chromatographed on silica gel using 10% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-bdb7dff8312e4908a4f1d50814af389d
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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