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

HRID 1440645Notes

Reaction equation

HRID 1440645 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, 2 mL 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)-l,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 (C18H18OS) m+ /z 316.

Workup

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

Sources & evidence

ORD record
ord-d9b3f8858d8e4be5b30abc04e913fd07
Source dataset
uspto-grants-1996_03
Patent number
US05500317

Reaction notes

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