Sodium hydride → Methyl beta-(2-methoxypyridin-5-yl)acrylate

HRID 53203

Reaction equation

HRID 53203 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][N:19]=1>C1(C)C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:11][C:12]([O:14][CH3:15])=[O:13])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 53929170Methyl beta-(2-methoxypyridin-5-yl)acrylateYield 85.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A suspension of 0.65 g (1.1 eq) of 95% NaH in 22 ml of toluene was slowly added to 3.8 g (1 eq) of methyl diethylphosphonoacetate in 5 ml of dry toluene below 35° C. The clear yellow solution was allowed to stir under nitrogen at room temperature for 30 min and a solution of 2.5 g (18.2 mmol) of 2-methoxy-pyridine-5-carboxaldehyde in 10 ml of toluene was added dropwise while maintaining the reaction temperature below 40° C. After the addition, the mixture was heated at 65° C. for 30 min, cooled, and filtered through solka floc and concentrated in vacuo to yield 3 g (85.7%) of methyl β-(2-methoxypyridin-5-yl)acrylate (cis/trans mixture).

Workup

  1. temperaturewhile maintaining the reaction temperature below 40° C
  2. additionAfter the addition
  3. temperaturethe mixture was heated at 65° C. for 30 min
  4. temperaturecooled
  5. filtrationfiltered through solka floc
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d607190a5ee4721af46fa3f7a63aa19
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Linked notes

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