Acetone → 1,5-Bis(2-thienyl)-1,4-pentadien-3-one

HRID 714186Notes

Reaction equation

HRID 714186 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH3:8][C:9]([CH3:11])=[O:10].[OH-].[Na+].O>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:8][C:9](=[O:10])[CH:11]=[CH:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 73642-ThiophenecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 7372011,5-Bis(2-thienyl)-1,4-pentadien-3-oneYield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Thiophenecarboxaldehyde (33, 0.50 ml, 5.3 mmol) and acetone (19, 0.20 ml, 2.7 mmol) were combined in ethanol (10 ml) and stirred for 10 min at room temperature. A solution of sodium hydroxide (0.30 g, 7.5 mmol) and water (10 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethanol/water to give 0.55 g (82%) of a yellow solid: mp 115-117° C. [expected mp 115-117° C.]; 1H NMR: δ 6.80 (d, 2H, J=15.5 Hz), 7.06 (dt, 2H, J=3.6, 1.4 Hz), 7.31 (d, 2H, J=3.4 Hz), 7.39 (d, 2H, J=5.0 Hz), 7.82 (d, 2H, J=15.5 Hz); 13C NMR: δ 124.4, 128.2, 128.7, 131.7, 135.5, 140.2, 187.5.

Workup

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-6ae2cff600ad49efb4c4ea55824a9696
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

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