Water → (E)-3-(3-nitrophenyl)-2-buten-1-ol
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[C:10](/[CH3:17])=[CH:11]/[C:12](OCC)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6](/[C:10](/[CH3:17])=[CH:11]/[CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a solution of ethyl (E)-3-(3-nitrophenyl)-2-butenoate (Preparation 1, 102 g, 0.43 mol) in toluene (1400 ml) at −10° C. under nitrogen was added dropwise over 3 h diisobutylaluminium hydride (1.0 M in toluene, 1 l), then the mixture was stirred at 0° C. for 1 h. Water (400 ml) was carefully added, followed by sodium hydrogen carbonate (300 g). The resulting slurry was vigorously stirred for 10 min, then ethyl acetate (2 l) was added, and the mixture stirred for 1 h. The mixture was dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a pale brown oil (81 g, 97%).
Workup
- stirringThe resulting slurry was vigorously stirred for 10 min
- stirringthe mixture stirred for 1 h
- dry with materialThe mixture was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-586b3b8460444d30bb705af9eacb6e8e
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07049444B2
Reaction notes
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