Sodium hydride → 3-(5-Dimethoxymethyl-pyridin-2-yl)-acrylic acid tert-butyl ester

HRID 556288Notes

Reaction equation

HRID 556288 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]=O)=[N:8][CH:9]=1.C(OP([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(OCC)=O)C.[H-].[Na+]>C1COCC1>[C:26]([O:25][C:23](=[O:24])[CH:22]=[CH:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]([O:12][CH3:13])[O:2][CH3:1])=[CH:9][N:8]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 184267805-(Dimethoxymethyl)picolinaldehyde

Product 1

HCID 669915493-(5-Dimethoxymethyl-pyridin-2-yl)-acrylic acid tert-butyl esterYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-dimethoxymethyl-pyridine-2-carbaldehyde (355 mg, 1.97 mmol) was dissolved in THF (10 ml) and the resulting solution was added to a stirring mixture of tert-butyl diethylphosphonoacetate (547 mg, 2.169 mmol) and NaH (102 mg, 2.56 mmol, 60% oil dispersion) in THF (5 ml). After 15 minutes the reaction was quenched by addition of water and the resulting slurry was extracted with Et2O. The organic phase was dried over Na2SO4 and evaporated under vacuo. The crude product was purified by silica gel chromatography (petroleum ether/EtOAc 95:5) to give 491 mg of 3-(5-dimethoxymethyl-pyridin-2-yl)-acrylic acid tert-butyl ester.

Workup

  1. customAfter 15 minutes the reaction was quenched by addition of water
  2. extractionthe resulting slurry was extracted with Et2O
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated under vacuo
  5. customThe crude product was purified by silica gel chromatography (petroleum ether/EtOAc 95:5)

Sources & evidence

ORD record
ord-c31129342cb643c5949596364b4a115f
Source dataset
uspto-grants-2011_11
Patent number
US08058273B2

Reaction notes

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