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

HRID 1506985노트

반응식

HRID 1506985 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-800707e93af84eb7a01aca1bb8412dd9
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221783B2

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