Sodium hydride → Methyl 2-[2-(3,4-diethoxyphenyl)thiazole-4-ylmethyl]-3-(3-ethoxypyridine-2-yl)-3-oxopropionate

HRID 2097556Notes

Reaction equation

HRID 2097556 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4].[CH2:26]([O:28][C:29]1[C:30]([C:35](OC)=[O:36])=[N:31][CH:32]=[CH:33][CH:34]=1)[CH3:27].[Cl-].[NH4+]>C(COC)OC.CO>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][CH:21]([C:35]([C:30]3[C:29]([O:28][CH2:26][CH3:27])=[CH:34][CH:33]=[CH:32][N:31]=3)=[O:36])[C:22]([O:24][CH3:25])=[O:23])[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12225781Methyl 3-ethoxypyridine-2-carboxylateHCID 68710823HCID 68710823, compound

Product 1

HCID 68710135Methyl 2-[2-(3,4-diethoxyphenyl)thiazole-4-ylmethyl]-3-(3-ethoxypyridine-2-yl)-3-oxopropionateYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (239 mg, 6.0 mmol) and a drop of methanol were added to a solution (10 ml) of methyl 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionate (1.0 g, 3.0 mmol) and methyl 3-ethoxypyridine-2-carboxylate (702 mg, 3.9 mmol) in dimethoxyethane, followed by heating under reflux for 2 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated salt solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/3). The solvent was distilled off under reduced pressure, to thereby obtain 740 mg (yield: 51%) of methyl 2-[2-(3,4-diethoxyphenyl)thiazole-4-ylmethyl]-3-(3-ethoxypyridine-2-yl)-3-oxopropionate as a yellow oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated salt solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/3)
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8a3a79923bd6449aa4b217b09387bb01
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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