Hexane → (2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

HRID 1607351

反応式

HRID 1607351 の反応式
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:14][OH:15].[CH3:16][C:17]1([CH3:27])[CH:19]([CH:20]=[C:21]([CH3:23])[CH3:22])[CH:18]1[C:24](Cl)=[O:25].CCCCCC>N1C=CC=CC=1.C(OCC)C>[CH3:16][C:17]1([CH3:27])[CH:19]([CH:20]=[C:21]([CH3:22])[CH3:23])[CH:18]1[C:24]([O:15][CH2:14][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]=1[CH3:1])=[O:25]

参加物

6

反応物 3

HCID 8058HexaneHCID 26620(1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chlorideHCID 596875[1,1'-Biphenyl]-3-methanol, 2-methyl-

生成物 1

HCID 13933694(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate収率 80.9%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 2.97 g (15.0 mmol) of (2-methyl-3phenylphenyl)methanol in 1.5 ml of pyridine and 10 ml of diethyl ether, was dropwise added to a solution of 2.80 g (15.0 mmol) of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride in 10 ml of diethyl ether, and the mixture was stirred at room temperature for 3 hours. After an addition of 20 ml of hexane thereto, the inorganic salt was filtered off, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography (silica gel, dichloromethane/hexane=1/2) to obtain 4.23 g of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate as a colorless oil.

後処理

  1. filtrationthe inorganic salt was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe product was purified by column chromatography (silica gel, dichloromethane/hexane=1/2)

出典と根拠

ORDレコード
ord-a77edb3fb18444be9245c48ecc90efb5
出典データセット
uspto-grants-1989_09
特許番号
US04864052

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