Ethyl Acetate → HCID 57082426, compound

HRID 985755Notes

Reaction equation

HRID 985755 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][S:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][CH2:22][C:23]2=O)=[CH:18][CH:17]=1.C(OCC)(=O)C>O1CCCC1>[CH3:14][S:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][CH2:22][C:23]2=[CH:3][C:1]#[N:2])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 21917078857995-47-2

Product 1

HCID 57082426HCID 57082426, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an inert atmosphere and at 0° C., diethyl cyanomethylphosphonate (7.6 ml, 46.8 mmol) is added dropwise to a suspension of sodium hydride (2.25 g, 46.8 mmol) in 50 ml of tetrahydrofuran. Stirring is carried out at 0° C. for 30 minutes; the compound obtained in Step C (6 g, 31.2 mmol), dissolved in 50 ml of tetrahydrofuran, is then added and the reaction mixture is stirred at ambient temperature for 3 hours. After hydrolysis and extraction with ethyl acetate, the organic phase is washed with water, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on silica gel (eluant: petroleum ether/dichloromethane 50/50) to yield the unsaturated nitrile of the title.

Workup

  1. additionis then added
  2. stirringthe reaction mixture is stirred at ambient temperature for 3 hours
  3. washthe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue is purified by chromatography on silica gel (eluant: petroleum ether/dichloromethane 50/50)

Sources & evidence

ORD record
ord-a9bf15cbeaf54d4ca017a3c9b6e8c17c
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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