Sodium hydride → Methyl (E)-3-(2-quinolinyl)-2-propenoate
Reaction equation
C(OP([CH2:9][C:10]([O:12][CH3:13])=[O:11])(OCC)=O)C.[H-].[Na+].[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[CH:26]=O>C1COCC1>[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1/[CH:26]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 2-(diethoxyphosphoryl)acetate (4.41 g, 20.9 mmol) in THF (8 mL) was added NaH (0.91 g, 22 mmol) and the resultant solution was stirred for 20 min. The reaction mixture was cooled to 0° C. and quinoline-2-carbaldehyde (3.0 g, 19 mmol) in THF (4 mL) was added via syringe. The reaction was allowed to warm to room temperature and stirred for 3 h. The reaction was quenched with saturated sodium bicarbonate (10 mL) and the resulting mixture was extracted with DCM (100 mL). The DCM layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue obtained was purified by flash column chromatography on silica gel (0-30% EtOAc-heptane) to afford compound 79a. Mass spectrum (LCMS, ESI pos.) Calcd. For C13H11NO2 214.1 (M+H). found 214.1.
Workup
- temperatureto warm to room temperature
- customThe reaction was quenched with saturated sodium bicarbonate (10 mL)
- extractionthe resulting mixture was extracted with DCM (100 mL)
- dry with materialThe DCM layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue obtained
- customwas purified by flash column chromatography on silica gel (0-30% EtOAc-heptane)
Sources & evidence
- ORD record
- ord-331b3399aaf94bd3956b475b12869507
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193736B2
Reaction notes
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