Hydrochloric Acid → HCID 53926632, compound

HRID 622746Notes

Reaction equation

HRID 622746 reaction equation
[H-].[Na+].C[C:4](P(OC)(O)=O)([C:6]([O-:8])=[O:7])[CH3:5].C([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:17]=1)=O.Cl.[CH3:30]N(C)C=O>>[O:22]([C:18]1[N:17]=[C:16]([CH:5]=[CH:4][C:6]([O:8][CH3:30])=[O:7])[CH:21]=[CH:20][CH:19]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 129410066-Phenoxypyridine-2-carbaldehydeHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 53926632HCID 53926632, compound

Procedure

Under a nitrogen atmosphere, 0.53 g of sodium hydride (60% oil dispersion) was added to 20 ml of dry dimethylformamide, and 2.77 g of trimethylphosphonoacetate were added dropwise over 5 minutes with ice-cooling. After dropwise addition, stirring was continued at room temperature for 30 minutes. A solution of 2.02 g of 2-formyl-6-phenoxypyridine in 5 ml of dry dimethylformamide was added dropwise thereto over 5 minutes with ice-cooling. After dropwise addition, stirring was continued at room temperature for 14 hours. The reaction solution was poured into ice water, neutralized to a pH of 6.8 with aqueous dilute hydrochloric acid, and then extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure, and the residue was column-chromatographed on silica gel (developing solvent, n-hexane:ethyl acetate=7.1) to obtain 2.1 g of the desired methyl 3-(6-phenoxypyridin-2-yl)propenate.

Workup

  1. additionwere added dropwise over 5 minutes with ice-
  2. temperaturecooling
  3. additionAfter dropwise addition
  4. temperatureover 5 minutes with ice-cooling
  5. additionAfter dropwise addition
  6. stirringstirring
  7. waitwas continued at room temperature for 14 hours
  8. extractionextracted twice with diethyl ether
  9. washwashed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was then removed by evaporation under reduced pressure
  12. customthe residue was column-chromatographed on silica gel (developing solvent, n-hexane:ethyl acetate=7.1)

Sources & evidence

ORD record
ord-d093c3487997402d91e687ff812d1af8
Source dataset
uspto-grants-1988_09
Patent number
US04772633

Reaction notes

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