Water → HCID 19972647, compound
Reaction equation
[OH:1][C:2]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([CH3:18])[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:26][CH2:27][CH2:28][CH2:29][CH2:30]Br.O>CN(C)C=O>[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][O:1][C:2]1[C:11]2[O:10][C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:8]([CH3:18])[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 5 g of 8-hydroxy-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran, 4.2 g of anhydrous potassium carbonate and 43.6 g of 1,4-dibromobutane in 45 ml of dimethylformamide was stirred at 75° C. for 2 hours. The mixture was cooled to 20°-25° C., poured into 100 ml of water and extracted with dichloromethane. The organic solution was washed with aqueous sodium chloride solution and dried on anhydrous sodium sulfate. The solvents and excess 1,4-dibromobutane were evaporated off in vacuo. The residue was rinsed with 55 ml of petroleum ether:diethyl ether (7:4) and collected by suction filtration to yield 5.6 g of the title compound, m.p. 91°-92° C.
Workup
- temperatureThe mixture was cooled to 20°-25° C.
- extractionextracted with dichloromethane
- washThe organic solution was washed with aqueous sodium chloride solution
- dry with materialdried on anhydrous sodium sulfate
- customThe solvents and excess 1,4-dibromobutane were evaporated off in vacuo
- washThe residue was rinsed with 55 ml of petroleum ether:diethyl ether (7:4)
- filtrationcollected by suction filtration
Sources & evidence
- ORD record
- ord-688e74ae450b429bbe3967872fcd3048
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05605896
Reaction notes
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