Styrene → Ethyl trans-2-phenylcyclopropanecarboxylate

HRID 1485081

반응식

HRID 1485081 반응식
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>ClCCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[C:3]1([C@@H:2]2[CH2:1][C@H:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:3]1([C@H:2]2[CH2:1][C@H:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 2

HCID 7501StyreneHCID 12192Ethyl diazoacetate

생성물 2

HCID 252496Ethyl trans-2-phenylcyclopropanecarboxylateHCID 816743ethyl (1R,2S)-2-phenylcyclopropane-1-carboxylate

시약·촉매·용매 2

HCID 152122Dirhodium tetraacetate촉매HCID 111,2-Dichloroethane용매2회

실험 절차

To a suspension of styrene (3.00 g) and rhodium(II) acetate dimer (40.0 mg) in 1,2-dichloroethane (29.0 mL), a solution of ethyl diazoacetate (3.03 mL) in 1,2-dichloroethane (29.0 mL) was added over a period of 4 hours and the mixture was stirred at room temperature for 19 hours. The reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane:diethyl ether=20:1) to give ethyl trans-2-phenylcyclopropanecarboxylate as a colorless oil (2.42 g) and ethyl cis-2-phenylcyclopropanecarboxylate as a colorless oil (1.51 g).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography (n-hexane:diethyl ether=20:1)

출처 및 근거

ORD 기록
ord-cd51802230054e0eb6a9d8fe7618ce9e
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422240B2

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