Water → HCID 86741940, compound

HRID 569149Notes

Reaction equation

HRID 569149 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=2)[CH:18]=1.O>O1CCCC1>[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:31]=[CH:30][C:27](/[CH:28]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:26][CH:25]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 46774194-(Pyridin-3-yloxy)benzaldehyde

Product 1

HCID 86741940HCID 86741940, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 6 ml of anhydrous tetrahydrofuran was suspended 700 mg of sodium hydride (purity: 50%), and into the suspension was dropped a mixture of 3.65 g of ethyl diethylphosphonoacetate and 3 ml of anhydrous tetrahydrofuran at a temperature of 30° to 35° C., after which the resulting mixture was subjected to reaction at room temperature for one hour. To the reaction mixture was added dropwise a mixture of 3.0 g of 4-(pyridin-3-yloxy)benzaldehyde and 3 ml of anhydrous tetrahydrofuran at room temperature, and the temperature thereof was gradually elevated. The mixture was subjected to reaction at 60° C. for 15 minutes. Subsequently, the reaction mixture was cooled to room temperature, and 20 ml of water was added to the mixture, after which the resulting mixture was subjected to extraction with 20 ml of ethyl acetate. The extract was washed with 10 ml of a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform], to obtain 3.64 g (yield 89.8%) of colorless, oily ethyl (E)-3-[4-(pyridin-3-yloxy)phenyl]acrylate.

Workup

  1. additioninto the suspension was dropped
  2. customafter which the resulting mixture was subjected to reaction at room temperature for one hour
  3. additionTo the reaction mixture was added dropwise
  4. customThe mixture was subjected to reaction at 60° C. for 15 minutes
  5. extractionafter which the resulting mixture was subjected to extraction with 20 ml of ethyl acetate
  6. washThe extract was washed with 10 ml of a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customafter which the solvent was removed by distillation under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform]

Sources & evidence

ORD record
ord-984623f4e8f942beb9998fda7af5df73
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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