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

HRID 1805943ノート

反応式

HRID 1805943 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 110640761,3-Oxathiolane-2-methanol, 2-benzoate収率 80%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-53ff4a43a6b74b6b8d0210107491c08e
出典データセット
uspto-grants-2013_01
特許番号
US08354546B2

反応ノート

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