Acetic Acid → HCID 3666021, compound

HRID 2295235Notes

Reaction equation

HRID 2295235 reaction equation
[O-]CC.[Na+].[C:5]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)(=[O:7])[CH3:6].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.C(O)(=O)C>CCO>[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[O:7])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69202-AcetylthiopheneHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 3666021HCID 3666021, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium ethoxide (21% by weight in EtOH, 0.68 gm, 10 mmol) was added to a solution of 2-acetylthiophene (12.60 gm, 100 mmol, from Aldrich) and 4-fluorobenzaldehyde (12.41 gm, 100 mmol, from Aldrich) in EtOH (50 ml) and the mixture stirred under argon for 15 minutes. More EtOH (25 ml) was then added to make a slurry of the reaction mixture, which had partially solidified. Acetic acid (0.60 gm, 11 mmol) was added and a yellow solid filtered out of solution. The solid was recrystallized from EtOAc and hexane to afford the title compound as long, pale yellow needles (17.679 gm, 71%).

Workup

  1. filtrationa yellow solid filtered out of solution
  2. customThe solid was recrystallized from EtOAc and hexane

Sources & evidence

ORD record
ord-93e983cc0a8e4b8e8dcabe7c4b9f2982
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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