Dimethylformamide → Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate
Reaction equation
CN(C)C=O.CC(C)([O-])C.[Na+].[CH3:12][CH2:13][O:14][C:15]([CH:17](P(OCC)(OCC)=O)[CH3:18])=[O:16].[CH3:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1>O>[CH3:18][C:17](=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([CH3:27])=[CH:29][CH:30]=1)[C:15]([O:14][CH2:13][CH3:12])=[O:16]Participants
6
Conditions
- Temperature
- -2.5 °C
Procedure
To dimethylformamide (1802 ml) that had been cooled to −10° C. was added sodium tert-butoxide (528.6 g) and the solution was stirred at −5 to 0° C. for 30 min. Triethyl 2-phosphonopropionate (1310 g) was added dropwise thereto at 10° C. or below. The solution was stirred at 2 to 5° C. for 1 hr, and 4-methylbenzaldehyde (600.8 g) was added dropwise thereto at 10° C. or below and the solution was stirred at room temperature for 1 hr. Water was added thereto and the solution was extracted with toluene. The extract was washed with water and the solvent was distilled off to give the title compound as an oil (1009 g, yield 98.8%).
Workup
- customat 10° C. or below
- stirringThe solution was stirred at 2 to 5° C. for 1 hr
- stirringat 10° C. or below and the solution was stirred at room temperature for 1 hr
- extractionthe solution was extracted with toluene
- washThe extract was washed with water
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-89afea3efcbc45399654fa901a6248e4
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06878831B2
Reaction notes
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