Methanol → 2-Furoylacetonitrile

HRID 568590Notes

Reaction equation

HRID 568590 reaction equation
C(O[C:4]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)=[O:5])C.[H-].[Na+].[C:13](#[N:15])[CH3:14].CO>C1(C)C=CC=CC=1>[O:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4]([CH2:14][C:13]#[N:15])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 6342AcetonitrileHCID 11980Ethyl 2-furoateHCID 24758Sodium hydride

Product 1

HCID 1416712-FuroylacetonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

63.05 grams (0.5 mole) of furan-2-carboxylic acid ethyl ester and 30.0 grams (1 mole) of sodium hydride (80 weight % suspension in white oil) were reacted with 41 grams (1 mole) of acetonitrile in 500 ml of toluene with the addition of 1 ml of methanol at 90° C. After 3 hours reaction time the toluene was distilled off, the residue stirred with 500 ml of water, acidified with hydrochloric acid to pH 1.5 and the precipitated product filtered off with suction and recrystallized from methanol. There were obtained 51.3 grams (76% of theory) of 2-furanoylacetonitrile having a melting point of 74°-75° C.

Workup

  1. distillationwas distilled off
  2. filtrationthe precipitated product filtered off with suction
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8292bec4055745558c0380a92dd578d4
Source dataset
uspto-grants-1988_03
Patent number
US04728743

Reaction notes

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