Sodium hydride → HCID 54229760, compound

HRID 1031503Notes

Reaction equation

HRID 1031503 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:13])(OCC)=O)C.[Cl:20][C:21]1[CH:45]=[CH:44][CH:43]=[CH:42][C:22]=1[O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=O)[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)=[CH:26][N:25]=1>COCCOC>[Cl:20][C:21]1[CH:45]=[CH:44][CH:43]=[CH:42][C:22]=1[O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)=[CH:11][C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11207805Phosphonic acid, [2-(4-morpholinyl)-2-oxoethyl]-, diethyl esterHCID 14878846HCID 14878846, compound

Product 1

HCID 54229760HCID 54229760, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

In 1,2-dimethoxyethane (10 ml) was suspended 60% sodium hydride (dispersion in paraffin) (132 mg). To the suspension was added dropwise, while stirring, a solution of diethylphosphonoacetic acid morpholide (688 mg) in 1,2-dimethoxyethane (5 ml). To the mixture was added 2-(2-chlorophenoxy)-5-(3,4-dimethoxybenzoyl)pyridine (800 mg), which was heated for 8 hours under reflux. The reaction mixture was concentrated and the residue was dissolved in ether, washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off to leave an oily substance, which was purified by means of a silica gel chromatography (eluted with ethyl acetate) to obtain 4-[3-(2-(2-chlorophenoxy)-5-pyridyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine (Compound No.1) (330 mg) as a resinous solid.

Workup

  1. additionTo the suspension was added dropwise
  2. temperaturewas heated for 8 hours
  3. temperatureunder reflux
  4. concentrationThe reaction mixture was concentrated
  5. dissolutionthe residue was dissolved in ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was then distilled off
  9. customto leave an oily substance, which
  10. customwas purified by means of a silica gel chromatography (eluted with ethyl acetate)

Sources & evidence

ORD record
ord-b1d6e2d05cab486c9ad94dfadc2dbe51
Source dataset
uspto-grants-1990_09
Patent number
US04954497

Reaction notes

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