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

HRID 1689576Notes

Reaction equation

HRID 1689576 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 HPLC. 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 HPLC
  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-af9888e577624391be59c7d94f32cff9
Source dataset
uspto-grants-2012_04
Patent number
US08153416B2

Reaction notes

Loading…