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

HRID 453770ノート

反応式

HRID 453770 の反応式
[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

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86644716HCID 86644716、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7af6c09541bf4a279d84b60eb62fac2f
出典データセット
uspto-grants-2013_07
特許番号
US08492549B2

反応ノート

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