Sodium Bicarbonate → tert-Butyl (E)-3-(5-formyl-pyridin-2-yl)-acrylate

HRID 885838Notes

Reaction equation

HRID 885838 reaction equation
[C:1]([O:5][C:6](=[O:20])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH:15](OC)[O:16]C)=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>C1COCC1.Cl>[C:1]([O:5][C:6](=[O:20])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 44820265tert-Butyl (E)-3-(5-dimethoxymethyl-pyridin-2-yl)-acrylate

Product 1

HCID 44819897tert-Butyl (E)-3-(5-formyl-pyridin-2-yl)-acrylateYield 98.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-3-(5-dimethoxymethyl-pyridin-2-yl)-acrylic acid tert-butyl ester (1.76 mg, 6.30 mmol) in THF (30 ml) and 1 M HCl (25 ml) was stirred for 4 hours at room temperature, then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with Et2O. The pooled organic phases were dried over Na2SO4 and evaporated in vacuo to dryness to give 1.45 g of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester as a white solid.

Workup

  1. extractionextracted twice with Et2O
  2. dry with materialThe pooled organic phases were dried over Na2SO4
  3. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-2e7c881402de4d3785d0f347f2e37aa3
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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