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

HRID 2169244ノート

反応式

HRID 2169244 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-690b8e5404024846af0d182fbc77e65a
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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