1,2-Dichloroethane → (4-Chloro-phenyl)-acetic acid pent-2-enyl ester

HRID 733314ノート

反応式

HRID 733314 の反応式
[CH2:1]([OH:6])/[CH:2]=[CH:3]/[CH2:4][CH3:5].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](O)=[O:16])=[CH:10][CH:9]=1.C(Cl)CCl>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:6][C:15](=[O:16])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)[CH:2]=[CH:3][CH2:4][CH3:5]

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 15880(4-Chlorophenyl)acetic acidHCID 53649202-Penten-1-ol

生成物 1

HCID 68576441(4-Chloro-phenyl)-acetic acid pent-2-enyl ester収率 116.8%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Trans-2-penten-1-ol (49.6 ml; 487.6 mmol) and (4-chloro-phenyl)-acetic acid (83.2 g; 487.6 mmol) were dissolved in 1200 ml of dichloromethane. After addition of EDC (140.2 g, 731 mmol) and DMAP (11.9 g, 97.5 mmol), the reaction mixture was stirred for 18 hours at room temperature. After evaporation under reduced pressure, the residue was dissolved with diethyl ether, washed with water, brine and dried over anhydrous sodium sulfate. Evaporation gave 136 g of an yellow oil, which was further purified by flash-chromatography (silica gel; hexane/ethyl acetate 9:1). Yield: 68 g (59%).

後処理

  1. customAfter evaporation under reduced pressure
  2. dissolutionthe residue was dissolved with diethyl ether
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation

出典と根拠

ORDレコード
ord-9256b286bea844feaed9660f548a8edf
出典データセット
uspto-grants-2009_09
特許番号
US07589091B2

反応ノート

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