Sodium hydride → HCID 178445048, compound
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19](Cl)(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[C:19]([C:13](=[CH:12][NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH3:3])[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
50% Sodium hydride (4.8 g, 0.1 mol) was washed with petroleum ether and then suspended under nitrogen in dry tetrahydrofuran (50 ml) at -30° C. Ethyl 3-(2-methoxyphenylamino)acrylate (17.4 g, 0.1 mol) in dry tetrahydrofuran (100 ml) was added dropwise to the stirred suspension keeping the temperature below -20° C. Cooling was removed and the mixture was stirred until a deep red colour was obtained. The mixture was re-cooled to -30° C. and hexanoyl chloride (13.8 ml, 0.1 mol) in dry tetrahydrofuran (50 ml) was added dropwise. Cooling was again removed and the mixture was stirred for 2 hours. The mixture was partitioned between 10% hydrochloric acid and dichloromethane then washed with water and brine, dried and evaporated to afford an oil which was chromatographed (silica gel, chloroform) to give ethyl 2-hexanoyl-3-(2-methoxyphenyl- amino)acrylate, (20 g, 62.7%).
Workup
- customthe temperature below -20° C
- temperatureCooling
- customwas removed
- customwas obtained
- temperatureCooling
- customwas again removed
- stirringthe mixture was stirred for 2 hours
- customThe mixture was partitioned between 10% hydrochloric acid and dichloromethane
- washthen washed with water and brine
- customdried
- customevaporated
- customto afford an oil which
- customwas chromatographed (silica gel, chloroform)
Sources & evidence
- ORD record
- ord-521d234caa3d4f28ac0bcd875d62f282
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806549
Reaction notes
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