Sodium hydride → (E)-3-(7-Fluoro-benzofuran-4-yl)-acrylonitrile

HRID 1602395Notes

Reaction equation

HRID 1602395 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[F: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.[Cl-].[NH4+]>COCCOC.C(OCC)(=O)C>[F: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 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 19611665HCID 19611665, compound

Product 1

HCID 19611668(E)-3-(7-Fluoro-benzofuran-4-yl)-acrylonitrile

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of diethyl cyanomethylphosphonate (5.35 g) in dry ethylene glycol dimethyl ether (DME; 20 ml) was added to a suspension of sodium hydride (60% oil dispersion; 1.32 g) in DME (20 ml) at 0° under nitrogen over 5 mins. After 15 min, a solution 7-fluoro-benzofuran-4-carbaldehyde (4.51 g) in DME (20 ml) was added and after 5 mins the solution was warmed up and stirred at room temperature for 2 h. Ammonium chloride solution (200 ml) and ethyl acetate (150 ml) were added, the phases separated and the aqueous extracted with ethyl acetate (2×150 ml). The extracts were dried (MgSO4) and evaporated and the residue triturated under ether (20 ml) and filtered to give the E isomer as a buff coloured solid (3.07 g)

Workup

  1. temperaturewas warmed up
  2. customthe phases separated
  3. extractionthe aqueous extracted with ethyl acetate (2×150 ml)
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated
  6. customthe residue triturated under ether (20 ml)
  7. filtrationfiltered
  8. customto give the E isomer as a buff

Sources & evidence

ORD record
ord-ea3229a34eee42c7a085b26c70a9716e
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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