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

HRID 733314노트

반응식

HRID 733314 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9256b286bea844feaed9660f548a8edf
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589091B2

반응 노트

불러오는 중…