Water → Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

HRID 1739458노트

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HRID 1739458 반응식
[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].O.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)([O:5][CH2:4][C@H:2]1[O:3][CH2:1]1)(=[O:15])=[O:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 5460455(+)-Glycidol

생성물 1

HCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-수율 78.4%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
2.5 °C

실험 절차

To a solution of 6.7 g of (R)-glycidol (0.09 mol)(optical purity: 99.4% ee) and 50 ml of water, 0.17 g of N,N-dimethylaminopyridine (0.0014 mol) and 17.2 g of p-toluenesulfonyl chloride (0.09 mol) in 50 ml of toluene, and then 18.1 g of 24% sodium hydroxide (0.11 mol) were added under stirring at 0-5° C. And the solution was stirred for one hour. After separation with a separating funnel, the organic layer was washed with 50 ml of 1% hydrochloric acid and 50 ml of water. The excess solvent was removed under vacuo. The chemical purity by HPLC and optical purity at that time were 99.5%, 99.5% ee respectively. The residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V) to give 16.1 g of (S)-glycidyl tosylate (yield 78%). Chemical purity: 99.9%, Optical purity: 99.6% ee

후처리

  1. stirringAnd the solution was stirred for one hour
  2. customAfter separation with a separating funnel
  3. washthe organic layer was washed with 50 ml of 1% hydrochloric acid and 50 ml of water
  4. customThe excess solvent was removed under vacuo
  5. customThe residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V)

출처 및 근거

ORD 기록
ord-1c27e472bd4c491cbd453d9000b8bede
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965753

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