Benzoyl chloride → 2(S)-(benzoyloxymethyl)-1,3-oxathiolane

HRID 1689575노트

반응식

HRID 1689575 반응식
[OH:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[C:8]([O:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 46244897HCID 46244897, 화합물

생성물 1

HCID 596089912(S)-(benzoyloxymethyl)-1,3-oxathiolane수율 44.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2(S)-(Hydroxymethyl)-1,3-oxathiolane (0.25 mmol, 30 mg, 1.0 equiv.) recovered from Example 3 was treated with benzoyl chloride (0.25 mmol, 35 mg, 1.0 equiv.), triethylamine (0.25 mmol, 25 mg, 1.0 equiv.) in dichloromethane (1 mL) at ambient temperature while monitoring the reaction progress by TLC. After 1 h, the reaction was extracted with saturated ammonium chloride solution and brine. The organic phase was concentrated and chromatographed on silica gel to give 2(S)-(benzoyloxymethyl)-1,3-oxathiolane (25 mg, 44.6%).

후처리

  1. extractionthe reaction was extracted with saturated ammonium chloride solution and brine
  2. concentrationThe organic phase was concentrated
  3. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-2b1d43f87cb148e4864d59d7e1a195a5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153416B2

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