p-Toluenesulfonic acid monohydrate → 1,3-Oxathiolane-2-methanol, 2-benzoate

HRID 1805943Notes

Reaction equation

HRID 1805943 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]1[S:15][CH2:14][CH2:13][O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:9][CH2:10][CH:11]1[S:15][CH2:14][CH2:13][O:12]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 596089912(S)-(benzoyloxymethyl)-1,3-oxathiolane

Product 1

HCID 110640761,3-Oxathiolane-2-methanol, 2-benzoateYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2(S)-(Benzoyloxymethyl)-1,3-oxathiolane (0.045 mmol, 10 mg, 1.0 equiv.), para-toluenesulfonic acid monohydrate (0.015 mmol, 3 mg, 0.3 equiv.) and toluene (1 mL) were heated to reflux and stirred while monitoring the racemization reaction by chiral HLPC. After 24 h, the reaction was allowed to cool to ambient temperature and washed with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated by rotary evaporation to give 8 mg (80% yield) of (+/−)-2-(benzoyloxymethyl)-1,3-oxathiolane.

Workup

  1. temperatureto reflux
  2. customthe racemization reaction by chiral HLPC
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-53ff4a43a6b74b6b8d0210107491c08e
Source dataset
uspto-grants-2013_01
Patent number
US08354546B2

Reaction notes

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