m-Chloroperbenzoic acid → Acetic acid 5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

HRID 2407264노트

반응식

HRID 2407264 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C@H:20]2[CH2:22][O:21]2)=[C:13](C(=O)C)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=[C:26]([C:30]([O:32]O)=[O:31])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C@H:20]2[CH2:22][O:21]2)=[C:13]([O:32][C:30](=[O:31])[CH3:26])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86644716HCID 86644716, 화합물

생성물 1

HCID 86644717Acetic acid 5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester수율 52.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 1-[5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanone (1.0 g, 3.36 mmol) in DCM (20 ml) was added m-chloroperbenzoic acid (1.24 g) and solid NaHCO3 (3.24 g). The mixture was stirred at RT for 3 d. The mixture was filtered and the filtrate washed once with 10% NaHSO4 solution and then twice with NaHCO3 solution. The organic layer was washed with water and brine and dried with Na2SO4. The solvent was removed under reduced pressure. The residue was triturated with ether to give the title compound (0.55 g) as a white solid, which was used without purification.

후처리

  1. filtrationThe mixture was filtered
  2. washthe filtrate washed once with 10% NaHSO4 solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was triturated with ether

출처 및 근거

ORD 기록
ord-6440fab3bd1c423c95a8fd5797d8c7ca
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809536B2

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