Sodium hydride → HCID 54176212, compound

HRID 868355Notes

Reaction equation

HRID 868355 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]=O)=[N:14][CH:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CN(C)C=O>[C:3]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]=[CH:10][C:8]([O:7][CH2:3][CH3:4])=[O:9])=[N:14][CH:15]=1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21288007HCID 21288007, compound

Product 1

HCID 54176212HCID 54176212, compoundYield 186.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.2 g of triethyl phosphonoacetate in 20 ml of dimethylformamide, 0.39 g of sodium hydride (about 60%, in oil) is added slowly, and then 2.0 g of 5-t-butoxycarbonyl-2-pyridinecarbaldehyde is added. The resulting mixture is stirred at room temperature overnight and concentrated, and 20 ml of water is added. The aqueous solution is extracted with three 40-ml portions of chloroform. The combined extracts are dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel with chloroform to give 2.5 g of ethyl 3-(5-t-butoxycarbonyl-2-pyridyl)acrylate.

Workup

  1. concentrationconcentrated
  2. addition20 ml of water is added
  3. extractionThe aqueous solution is extracted with three 40-ml portions of chloroform
  4. dry with materialThe combined extracts are dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel with chloroform

Sources & evidence

ORD record
ord-27037803e5324e20a23f6c9031307747
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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