Water → 2-Thenoylacetonitrile

HRID 2049309Notes

Reaction equation

HRID 2049309 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]CC)=O.CC(C)([O-])C.[K+].[C:17](#[N:19])[CH3:18].O>C(Cl)Cl>[O:8]=[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:18][C:17]#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 76052Ethyl 2-thenoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 1418532-Thenoylacetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 67 ml. portion of ethyl 2-thiophenecarboxylate is added to 56 g. of potassium t-butoxide (exothermic). After cooling, 33 ml. of acetonitrile is added and the mixture is stirred and heated on a steam bath for 1.5 hours. A 250 ml. portion of water is added followed by 200 ml. of methylene chloride. The mixture is stirred overnight. The aqueous layer is separated and combined with 42 ml. of concentrated hydrochloric acid. This mixture is extracted with 300 ml. of methylene chloride followed by two 100 ml. portions of methylene chloride. The combined extracts are then washed with 200 ml. followed by 100 ml. of 10% sodium bicarbonate. The extracts are dried over sodium sulfate and passed through magnesol. The filtrate is combined with hexanes and evaporated giving crystals of β-oxo-2-thiophenepropionitrile.

Workup

  1. temperatureAfter cooling
  2. temperatureheated on a steam bath for 1.5 hours
  3. stirringThe mixture is stirred overnight
  4. customThe aqueous layer is separated
  5. extractionThis mixture is extracted with 300 ml
  6. washThe combined extracts are then washed with 200 ml
  7. dry with materialThe extracts are dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-de13b234a45a4e4aab956acc6cb50993
Source dataset
uspto-grants-1980_04
Patent number
US04197310

Reaction notes

Loading…