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

HRID 446760

反応式

HRID 446760 の反応式
[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]

参加物

5

反応物 2

HCID 9550DiazomethaneHCID 136011774-tert-Butylcinnamic acid ethyl ester

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7ba020a4d3a34f9290a331804c6f7c81
出典データセット
uspto-grants-2013_07
特許番号
US08481532B2

関連ノート

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