Ethyl Acetate → 1-(2,5-Dichloro-phenyl)-cyclopentanecarbaldehyde
Reaction equation
[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]1Participants
Procedure
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.
Workup
- customwas quenched with saturated potassium sodium tartarate solution very slowly
- extractionIt was extracted with dichloromethane
- washwashed with brine
- customdried
- concentrationconcentrated
- customto get the crude residue which
- customwas purified over nor mal silica gel (100-200 mesh) column chromatography
Sources & evidence
- ORD record
- ord-690b8e5404024846af0d182fbc77e65a
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045486B2
Reaction notes
Loading…