Ethyl diazoacetate → ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylate

HRID 1528873

반응식

HRID 1528873 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>C(Cl)Cl.C1(NN)C=CC=CC=1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu]>[CH2:16]([O:15][C:13]([C@@H:12]1[CH2:7][C@H:6]1[C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:14])[CH3:17]

참가 물질

6

반응물 2

HCID 12192Ethyl diazoacetateHCID 162634-Bromostyrene

생성물 1

HCID 66578655ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylate

시약·촉매·용매 3

HCID 7516Phenylhydrazine촉매HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-촉매HCID 6344Dichloromethane용매2회

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온도
40 °C

실험 절차

Copper(II) acetylacetonate (0.156 g, 0.6 mmol) was dissolved in CH2Cl2 (40 mL) then phenylhydrazine (3 drops, catalytic amount) was added. After 5 minutes, 4-bromostyrene (2.6 mL, 20 mmol) was added and the reaction was heated to 40° C. Ethyl diazoacetate (3.1 mL, 30 mmol) in CH2Cl2 (40 mL) was slowly added using a syringe pump. The reaction was stirred at 40° C. overnight then cooled and submitted to standard aqueous workup. The crude material was purified on silica gel (0-10% EtOAc in hexanes) two times to afford a separable mixture of two cyclopropyl isomers (cis- and trans-) and the less polar isomer was determined to be the title compound.

후처리

  1. temperaturethen cooled
  2. customThe crude material was purified on silica gel (0-10% EtOAc in hexanes) two times
  3. customto afford
  4. additiona separable mixture of two cyclopropyl isomers (cis- and trans-)

출처 및 근거

ORD 기록
ord-2b2737fdb7724d82a87c73e46ed606aa
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090573B2

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