Sodium hydride → Methyl (E)-3-(2-quinolinyl)-2-propenoate
Reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[CH:24]=O>O1CCCC1>[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1/[CH:24]=[CH:5]/[C:3]([O:2][CH3:1])=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of trimethyl phosphonoacetate (3.0 ml, 18.6 mmol) in tetrahydrofuran (40 ml) under argon atmosphere at 0° C., 60% sodium hydride in oil (0.73 g, 18.3 mmol) was added at once and the resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture, a solution of quinolin-2-carbaldehyde (1) (1.0 g, 6.2 mmol) in tetrahydrofuran (40 ml) was added. After stirring for 1 hour at room temperature, the reaction mixture was partitioned between ethyl acetate (150 ml) and 2N HCl (150 ml). The organic layer was separated, washed with water (100 ml), brine (50 ml), and dried (Na2SO4). The solvent was removed in vacuum and the residue was chromatographed on silica gel with chloroform-ethyl acetate (9:1) as eluent to give the title compound (1.07 g, 81%) as oil. 1H NMR (DMSO-d6, HMDSO), δ: 3.78 (3H, s); 7.11 (1H, d, J=16.0 Hz); 7.48-8.16 (5H, m); 7.81 (1H, d, J=16.0 Hz); 8.43 (1H, d, J=8.6 Hz).
Workup
- stirringAfter stirring for 1 hour at room temperature
- customthe reaction mixture was partitioned between ethyl acetate (150 ml) and 2N HCl (150 ml)
- customThe organic layer was separated
- washwashed with water (100 ml), brine (50 ml)
- dry with materialdried (Na2SO4)
- customThe solvent was removed in vacuum
- customthe residue was chromatographed on silica gel with chloroform-ethyl acetate (9:1) as eluent
Sources & evidence
- ORD record
- ord-de4d1a142acd43cc9992fb47c41aa58e
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071620B2
Reaction notes
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