Diazomethane → Ethyl 2-(4-tert-butylphenyl)cyclopropanecarboxylate

HRID 446760

반응식

HRID 446760 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:20])=[N-]>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:20][CH:12]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 9550DiazomethaneHCID 136011774-tert-Butylcinnamic acid ethyl ester

생성물 1

HCID 615698Ethyl 2-(4-tert-butylphenyl)cyclopropanecarboxylate수율 84%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매

반응 조건

온도
-40 °C

실험 절차

To a −40° C. solution of (E)-ethyl 3-(4-tert-butylphenyl)acrylate (1.0 g, 4.3 mol) in ether (20 mL), freshly prepared diazomethane was added dropwise over 10 minutes. Pd(OAc)2 (30 mg, 0.133 mol) was then added. The reaction mixture was stirred for another 10 min at −40° C., and then filtered through a pad of Celite® and precipitate washed with ether. The filtrate was concentrated in vacuo and the crude material was then purified via silica gel column chromatography to afford ethyl 2-(4-tert-butylphenyl)cyclopropanecarboxylate (0.9 g, 84%) as an oil.

후처리

  1. filtrationfiltered through a pad of Celite®
  2. customprecipitate
  3. washwashed with ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude material was then purified via silica gel column chromatography

출처 및 근거

ORD 기록
ord-7ba020a4d3a34f9290a331804c6f7c81
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481532B2

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