Ethyl Acetate → (E)-3-(7-Chloro-benzofuran-4-yl)-acrylonitrile

HRID 1602381Notes

Reaction equation

HRID 1602381 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH:24]=O)=[C:19]2[C:23]=1[O:22][CH:21]=[CH:20]2.C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[Cl:14][C:15]1[C:23]2[O:22][CH:21]=[CH:20][C:19]=2[C:18](/[CH:24]=[CH:3]/[C:1]#[N:2])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 19611677HCID 19611677, compound

Product 1

HCID 19611650(E)-3-(7-Chloro-benzofuran-4-yl)-acrylonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of diethyl cyanomethylphosphonate (7.34 g) in dry tetrahydrofuran (20 ml) was added to a suspension of sodium hydride (60% oil dispersion; 1.65 g) in THF (40 ml) over 5 mins with ice cooling. After 15 min, a solution of 7-chloro-benzofuran-4-carbaldehyde in THF (20 ml) was added and after 5 mins the solution was warmed up and stirred at room temperature for 2 h. Brine (40 ml) and ethyl acetate (40 ml) were added, the phases separated and the aqueous extracted with ethyl acetate (2×20 ml). The extracts were dried (MgSO4) and evaporated and the residue crystallised from ethanol to give off-white fluffy needles (2.95 g) of (E)-3-(7-Chloro-benzofuran-4-yl)-acrylonitrile.

Workup

  1. temperaturewas warmed up
  2. customthe phases separated
  3. extractionthe aqueous extracted with ethyl acetate (2×20 ml)
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated
  6. customthe residue crystallised from ethanol

Sources & evidence

ORD record
ord-6cc93cd264bd4c8684349fde2f1df3f6
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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