Hydrochloric Acid → HCID 66918321, compound
Reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12]P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].CC(C)([O-])C.[K+].[N+:38]([C:41]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:42]=1[CH:43]=O)([O-:40])=[O:39].Cl>C1COCC1>[N+:38]([C:41]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:42]=1[CH:43]=[CH:12][C:9]1[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:11][CH:10]=1)([O-:40])=[O:39]Participants
6
Procedure
To a solution of 4-methoxycarbonylphenylmethyltriphenylphosphine bromide (4.83 g) in THF (20 ml), potassium t-butoxide (600 mg) was added. The mixture was stirred for 1 hour at room temperature. To the reaction solution, 2-nitro-5-chlorobenzaldehyde (742 mg) was added at 0° C. The mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into diluted HCl. The mixture was extracted with hexane-AcOEt. The organic layer was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane-AcOEt) and recrystallization from the mixture solvent of hexane-AcOEt to give the title compound (680 mg) having the following physical data.
Workup
- stirringThe mixture was stirred for 30 minutes at room temperature
- extractionThe mixture was extracted with hexane-AcOEt
- washThe organic layer was washed
- customdried over and
- concentrationconcentrated under the reduced pressure
- customThe residue was purified on silica gel column chromatography (hexane-AcOEt) and recrystallization from the mixture solvent of hexane-AcOEt
Sources & evidence
- ORD record
- ord-265e72a5ba924cc9b190fc9240744a6b
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448290B1
Reaction notes
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