Ethyl Acetate → 1-(2,5-Dichloro-phenyl)-cyclopentanecarbaldehyde

HRID 2169244노트

반응식

HRID 2169244 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([C:14]#N)[CH2:13][CH2:12][CH2:11][CH2:10]1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=[O:28])C>ClCCl.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([CH:14]=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10]1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 754260371-(2,5-Dichlorophenyl)cyclopentane-1-carbonitrile

생성물 1

HCID 867258941-(2,5-Dichloro-phenyl)-cyclopentanecarbaldehyde수율 76.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

To a stirred solution of 1-(2,5-dichloro-phenyl)-cyclopentanecarbonitrile (198) (32 g, 133.891 mmol) in dichloromethane (350 mL), was added Diisobutylaluminiumhydrid (25% in toluene, 191.0 mL, mmol) for 1 h at −70° C. and the reaction mixture was stirred 2 h at the same temperature (silica TLC, 10% ethyl acetate in hexane, Rf=0.7) The reaction mixture was quenched with saturated potassium sodium tartarate solution very slowly and stirred at room temperature for 16 h. It was extracted with dichloromethane, washed with brine and dried, concentrated to get the crude residue which was purified over nor mal silica gel (100-200 mesh) column chromatography using gradient eluent 2-20% ethyl acetate in hexane to get 1-(2,5-dichloro-phenyl)-cyclopentanecarbaldehyde (199) (25 g, 76.8%), as colorless liquid.

후처리

  1. customwas quenched with saturated potassium sodium tartarate solution very slowly
  2. extractionIt was extracted with dichloromethane
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto get the crude residue which
  7. customwas purified over nor mal silica gel (100-200 mesh) column chromatography

출처 및 근거

ORD 기록
ord-690b8e5404024846af0d182fbc77e65a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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