Water → E,E-1-(p-isopropylphenyl)-5-(2-thienyl)-1,4-pentadien-3-one

HRID 53353Notes

Reaction equation

HRID 53353 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O.[OH-].[Na+].O>C(O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[C:12](=[O:14])/[CH:13]=[CH:20]/[C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 73642-ThiophenecarboxaldehydeHCID 14798Sodium HydroxideHCID 118198164-(4-Isopropylphenyl)but-3-en-2-one

Product 1

HCID 19962435E,E-1-(p-isopropylphenyl)-5-(2-thienyl)-1,4-pentadien-3-oneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.9 grams (0.042 mol) of E-4-(p-isopropylphenyl)-3-butene-2-one, 4.7 grams (0.042 mol) of 2-thiophene carboxaldehyde, 2mL of 10% sodium hydroxide, 30 mL of water, and 75 mL of ethanol was stirred at ambient temperature for 15 hours. The product was collected by filtration and air dried to give 10.2 grams (86% of theoretical yield) of E,E-1-(p-isopropylphenyl)-5-(2-thienyl)-1,4-pentadien-3-one as a yellow solid. Melting point was determined to be 100°-101° C. Proton nuclear magnetic resonance (1H NMR) was conducted in CDCl3: d 7.84 (d, 1H, J=16 Hz), 7.69 (d, 1H, J=16 Hz), 7.53 (AA'BB', 2H), 7.39 (m, 1H), 7.32 (m, 1H), 7.25 (AA'BB', 2H), 7.06 (dxd, 1H, J=3.6, 5 Hz), 6.96 (d, 1H, J=16 Hz), 6.87 (d, 1H, J=16 Hz), 2.90 (septet, 1H, J=7 Hz), 1.23 (d, 6H, J=7 Hz). Infrared spectroscopy was conducted using a KBr pellet: 2960, 1650, 1585, 1180, and 705 cm-1. Field desorption mass spectral analysis (FDMS) was consistent with the proposed formula (C18H18 0S) m+ /z 316.

Workup

  1. filtrationThe product was collected by filtration and air
  2. customdried

Sources & evidence

ORD record
ord-4337eacc71284eff8968719450232ca2
Source dataset
uspto-grants-1997_04
Patent number
US05618950

Reaction notes

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