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

HRID 323903Notes

Reaction equation

HRID 323903 reaction equation
[C:1]([O:6][CH2:7][CH:8](OCC)OCC)(=[O:5])[CH2:2][CH2:3][CH3:4].[SH:15][CH2:16][C:17]([OH:19])=[O:18].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:1]([O:6][CH2:7][CH:8]1[S:15][CH2:16][C:17](=[O:19])[O:18]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 6101p-Toluenesulfonic acidHCID 112641752,2-diethoxyethyl Butanoate

Product 1

HCID 11206498(5-oxo-1,3-oxathiolan-2-yl)methyl ButanoateYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A well-stirred solution of 28 (6.13 g, 30 mmol), mercaptoacetic acid (4.14 g, 3.13 ml, 45 mmol) and p-TsOH. H2O (60 mg, 0.31 mmol) in dry toluene was refluxed for 2 hours. Solvent was occasionally removed with a Dean-Stark trap, and fresh dry toluene was added. After cooling to room temperature, the reaction mixture was diluted with AcOEt (50 ml) and successively washed with: concentrated NaHCO3 (2×100 ml) and brine (2×100 ml), dried, filtered and evaporated to afford 25 (5.2 g, 25.5 mmol, 85%) as a yellow liquid that was used in the next step without any further purification.

Workup

  1. customSolvent was occasionally removed with a Dean-Stark trap, and fresh dry toluene
  2. additionwas added
  3. additionthe reaction mixture was diluted with AcOEt (50 ml)
  4. washsuccessively washed with: concentrated NaHCO3 (2×100 ml) and brine (2×100 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-75aea1be01bb4f449f826f3bd5869498
Source dataset
uspto-grants-2001_04
Patent number
US06215004B1

Reaction notes

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