Water → HCID 18427479, compound
Reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:15](=O)[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:11]=[CH:12][C:13]=1[Cl:14].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]([C:15](=[CH2:1])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:11]=[CH:12][C:13]=1[Cl:14]Participants
Procedure
1.75 g (49.0 mmole) of methyltriphenylphosphonium bromide and 5.50 g (49.0 mmole) of potassium t-butoxide were suspended in 200 ml of dried benzene, and the mixture was stirred at room temperature for 6 hours under a nitrogen atmosphere. At the end of this time, 8.50 g of methyl 4-(3,4-dichlorophenyl)-4-oxobutanoate [prepared as described in step (a) above] were dissolved in 40 ml of benzene, and the resulting solution was added to the reaction mixture. The mixture was then stirred for 1 hour. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and diethyl ether ranging from 19:1 to 23:2 by volume as the eluent, to give 4.20 g of the title compound as a pale orange oil.
Workup
- additionthe resulting solution was added to the reaction mixture
- stirringThe mixture was then stirred for 1 hour
- extractionextracted with ethyl acetate
- extractionThe organic extract
- dry with materialwas dried over anhydrous sodium sulfate
- customthe solvent was removed by distillation under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
- washa gradient elution method
Sources & evidence
- ORD record
- ord-4608511e4d0b45249833bc6e7f5b639f
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448247B1
Reaction notes
Loading…