Thioglycolic Acid → (5-oxo-1,3-oxathiolan-2-yl)methyl Butanoate

HRID 323905Notes

Reaction equation

HRID 323905 reaction equation
[C:1]([O:6][CH2:7][CH:8]=[O:9])(=[O:5])[CH2:2][CH2:3][CH3:4].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[SH:25][CH2:26][C:27](O)=[O:28]>C(Cl)Cl>[C:1]([O:6][CH2:7][CH:8]1[S:25][CH2:26][C:27](=[O:28])[O:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 98988312-Oxoethyl butyrate

Product 1

HCID 11206498(5-oxo-1,3-oxathiolan-2-yl)methyl ButanoateYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a well-stirred suspension of 24 (1.3 g, 10 mmol) and CSA (116 mg, 0.50 mmol) in dry DCM (10 ml) was slowly added a solution of mercaptoacetic acid (2.76 g, 2.08 ml, 30 mmol) in dry DCM (5 ml). The reaction was left at room temperature for 16 hours with stirring. The reaction mixture was diluted with DCM (20 ml) and successively washed with: concentrated NaHCO3 (3×30 ml) and brine (2×30 ml), dried, filtered and evaporated to afford 25 (0.9 g, 4.4 mmol, 44%) as a colorless syrup.

Workup

  1. washsuccessively washed with: concentrated NaHCO3 (3×30 ml) and brine (2×30 ml)
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-2c9bafdde7ba4f6ca496682d9e81a494
Source dataset
uspto-grants-2001_04
Patent number
US06215004B1

Reaction notes

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