Glyoxylic Acid → 3-Cyano-3-(2-thienyl)acrylic acid potassium salt

HRID 1268836Notes

Reaction equation

HRID 1268836 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].[C:9]([OH:13])(=[O:12])[CH:10]=O.CC(C)([O-])C.[K+:19]>CO>[K+:19].[C:7]([C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[CH:10][C:9]([O-:13])=[O:12])#[N:8]

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 728802-ThienylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 533966293-Cyano-3-(2-thienyl)acrylic acid potassium saltYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of thiophene-2-acetonitrile 20 (Aldrich, Milwaukee, Wis.) (80.6 g, 0.655 mol) in MeOH (1.3 L) was added glyoxylic acid (63.3 g, 0.688 mol). To the reaction solution was added portion-wise over 10 minutes potassium tert-butoxide (77.2 g, 0.688 mol). A nitrogen atmosphere was applied, and the solution was brought to reflux. After 6 h, the reaction was warmed to room temperature, filtered, and washed with copious amounts of MeOH. After drying under reduced pressure, 100 g of 21 as a white crystalline solid was obtained.

Workup

  1. temperatureto reflux
  2. filtrationfiltered
  3. washwashed with copious amounts of MeOH
  4. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-c8e6134923f54c32ad9f25ffa98f49f1
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

Loading…