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

HRID 443568

Reaktionsgleichung

Reaktionsgleichung von HRID 443568
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7809P-XyleneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e0139b248d0b49ca81f2a029ff22a260
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04260761

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