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Diethyl Ether → 2-Methyl-3-phenylbenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylate

HRID 1607366
ノート
印刷プレビュー

反応式

HRID 1607366 の反応式
[CH3:1][C:2]1([CH3:34])[CH:4]([CH:5](OC(=O)C)[C:6](Cl)([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]=1[CH3:33])=[O:18].C(OCC)C.CCCCC>CN(C=O)C.[Zn]>[CH3:1][C:2]1([CH3:34])[CH:4]([CH:5]=[C:6]([Cl:11])[C:7]([F:8])([F:9])[F:10])[CH:3]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:22]=1[CH3:33])=[O:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 8003PentaneHCID 13933704(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoro-propyl)cyclopropanecarboxylate

生成物 1

HCID 549012-Methyl-3-phenylbenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylate収率 95%

試薬・触媒・溶媒 2

HCID 23994
Zinc
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 38.4 mg (0.074 mmol) of the stereoisomer [RF 0.39 (CH2Cl2 /hexane=1/1)] of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoro-propyl)cyclopropanecarboxylate obtained in Example 11 and dissolved in 0.3 ml of DMF, 6 mg of zinc powder was added, and the mixture was stirred at 60° C. for 2.5 hours. After an addition of 2 ml of diethyl ether and 2 ml of pentane to the mixture, the inorganic salt was filtered off through a silica gel short column. The silica gel was washed with diethyl ether, and the organic layers were combined and concentrated under reduced pressure. The product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/2) to obtain 29.8 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropanecarboxylate as a colorless oily substance.

後処理

  1. filtrationthe inorganic salt was filtered off through a silica gel short column
  2. washThe silica gel was washed with diethyl ether
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/2)

出典と根拠

ORDレコード
ord-1d450ce8d5fd45079b87b63cb33d67fd
出典データセット
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04864052

反応ノート

読み込み中…

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