(Triphenylphosphoranylidene)acetonitrile → 2-(7-Methoxybenzofuran-2-yl)acetonitrile

HRID 1389136Notes

Reaction equation

HRID 1389136 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][C:8](=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:14]>CC1C=CC(C)=CC=1>[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH2:15][C:13]#[N:14])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 28181127-Methoxybenzofuran-3(2H)-one

Product 1

HCID 540718412-(7-Methoxybenzofuran-2-yl)acetonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A mixture of 14.16 g of 7-methoxy-3-benzofuranone, 39.4 g of cyanomethylenetriphenylphosphorane and 70 ml of p-xylene was heated at reflux under nitrogen for 16 hours. The solvent was removed, the solid washed repeatedly with ether and the product obtained on removal of the solvent from the ether washings sublimed (145° bath, 1 micron). Crystallization of the sublimate from 20 ml of isopropyl alcohol gave 11.06 g (69% yield) of 7-methoxy-3-benzofuranacetonitrile. Nmr spectrum (in CDCl3): τ2.4 (t, J=1-2 Hz, 1); 2.8-3.3 (m, 3); 6.0 (s, 3) and 6.3 (d, J=1-2 Hz, 2).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 16 hours
  3. customThe solvent was removed
  4. washthe solid washed repeatedly with ether
  5. customthe product obtained on removal of the solvent from the ether washings sublimed (145° bath, 1 micron)
  6. customCrystallization of the sublimate from 20 ml of isopropyl alcohol

Sources & evidence

ORD record
ord-aa1180ccb14c4a3881fd3f286817283b
Source dataset
uspto-grants-1981_01
Patent number
US04243668

Reaction notes

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