Sodium hydride → Methyl (E)-3-(2-quinolinyl)-2-propenoate

HRID 1993778Notes

Reaction equation

HRID 1993778 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

5

Reactant 3

HCID 24758Sodium hydrideHCID 796192-QuinolinecarboxaldehydeHCID 80029Trimethyl phosphonoacetate

Product 1

HCID 6479253Methyl (E)-3-(2-quinolinyl)-2-propenoateYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. stirringAfter stirring for 1 hour at room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate (150 ml) and 2N HCl (150 ml)
  3. customThe organic layer was separated
  4. washwashed with water (100 ml), brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuum
  7. customthe residue was chromatographed on silica gel with chloroform-ethyl acetate (9:1) as eluent

Sources & evidence

ORD record
ord-0d3b4699f730423082306588f67a9660
Source dataset
uspto-grants-2010_01
Patent number
US07652036B2

Reaction notes

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