Water → (E)-4-(4-(2,3-dihydro-3-oxo-6-pyridazinyl)phenyl)-3-butenoic acid
Reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[N:4][NH:3]1.[Cl-].[PH4+].CN(C)[CH:20]=[O:21].[CH3:23][C:24](C)([O-])C.[K+].[OH2:29]>>[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11](/[CH:12]=[CH:23]/[CH2:24][C:20]([OH:21])=[O:29])=[CH:10][CH:9]=2)=[N:4][NH:3]1Participants
Conditions
- Temperature
- -50 °C
Procedure
A mixture of 3.00 g of 4-(2,3-dihydro-3-oxo-6-pyridazinyl) benzaldehyde, 6.12 g of β-ethoxyethyltriphneyl phosphonium chloride and 50 ml of N,N-dimethylformamide was cooled to -50° C. and stirred. 20 ml of an N,N-dimethylformamide solution of 5.55 g of potassium tert-butoxide was dropped and the temperature was gradually raised to 0° C. After 2 hours, the temperature was elevated to a room temperature and stirring was conducted for further 10 hours. Iced water was added and the aqueous layer was washed with chloroform. The aqueous layer was adjusted to about pH 3 with hydrochloric acid and deposited solids were collected by filtration. They were recrystallized from 50% hydrous N,N-dimethylformamide to obtain 1.51 g of the above-captioned compound as pale orange powder (yield: 39%).
Workup
- temperaturethe temperature was gradually raised to 0° C
- customwas elevated to a room temperature
- stirringstirring
- waitwas conducted for further 10 hours
- washthe aqueous layer was washed with chloroform
- filtrationwere collected by filtration
- customThey were recrystallized from 50% hydrous N,N-dimethylformamide
Sources & evidence
- ORD record
- ord-5fd769e7150c42faa69bd3f2fc5fdf90
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05607953
Reaction notes
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