1-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane → 3-(3,4-Dichlorophenyl)-4-(imidazol-1-yl)butan-1-al
Reaction equation
[N:1]1([CH2:6][CH:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:8][CH:9]2OCC[O:10]2)[CH:5]=[CH:4][N:3]=[CH:2]1>Cl>[Cl:21][C:16]1[CH:15]=[C:14]([CH:7]([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:8][CH:9]=[O:10])[CH:19]=[CH:18][C:17]=1[Cl:20]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
5N Aqueous hydrochloric acid solution (100 ml) was added to an ice-cooled solution of 1-(imidazol-1-yl)-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane (11 g) (see Preparation 17) in tetrahydrofliran (100 ml). The mixture was allowed to warm slowly to room temperature and then left to stand for 24 hours. The tetrahydrofuran was removed under reduced pressure and the acidic phase extracted with dichloromethane (2×100 ml). The organic phases were combined, washed with brine and dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure to give the crude product which was chromatographed on silica gel eluting with a solvent gradient of 97.5:2.5 changing to 95:5, by volume, dichloromedane:methanol, to give 3-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al (4.4 g) as a viscous oil.
Workup
- waitleft
- customThe tetrahydrofuran was removed under reduced pressure
- extractionthe acidic phase extracted with dichloromethane (2×100 ml)
- washwashed with brine
- dry with materialdried over anhydrous sodium sulphate
- customThe solvent was removed under reduced pressure
- customto give the crude product which
- customwas chromatographed on silica gel eluting with a solvent gradient of 97.5:2.5 changing to 95:5, by volume, dichloromedane
Sources & evidence
- ORD record
- ord-7310b99bb09e43ec90f2c3c1d84d43f7
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06207678B1
Reaction notes
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