m-Chloroperbenzoic acid → (+/-)-2-(Benzyloxymethyl)-3-(2-chlorophenyl)oxirane

HRID 1506985ノート

反応式

HRID 1506985 の反応式
[CH2:1]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:24]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[O:24]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 90033540(E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene

生成物 1

HCID 90017867(+/-)-2-(Benzyloxymethyl)-3-(2-chlorophenyl)oxirane収率 71.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (E)-1-(3-(benzyloxy)prop-1-enyl)-2-chlorobenzene(Preparation example 367, 4.94 g, 22 mmole) in CH2Cl2 (110 mL) was added 3-chloroperoxybenzoic acid (70˜75%, 8 g, 33 mmole) portionwise at 0° C. The mixture was stirred for 18 hr at room temperature. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with sat′ NaHCO3, H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (4.3 g, 60˜80%).

後処理

  1. customconsumption of SM
  2. customThe reaction mixture was quenched with H2O at 0° C.
  3. extractionthen extracted with EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. customseparated
  6. washThe combined organic layer was washed
  7. dry with materialdried over MgSO4
  8. customevaporated under reduced pressure
  9. customThe crude compound was purified by silica ge column

出典と根拠

ORDレコード
ord-800707e93af84eb7a01aca1bb8412dd9
出典データセット
uspto-grants-2015_12
特許番号
US09221783B2

反応ノート

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