Terephthalaldehyde → 4-[(5-Ethyl-4-phenyl-thiophen-2-yl)-3-oxo-propenyl]-benzaldehyde

HRID 552284Notes

Reaction equation

HRID 552284 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].[CH:17](=O)[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1>C(O)C.Cl.C(O)(C)C.O>[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH:9]=[CH:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

7

Reactant 2

HCID 12173TerephthalaldehydeHCID 671661641-(5-Ethyl-4-phenyl-thiophen-2-yl)-ethanone

Product 1

HCID 866401734-[(5-Ethyl-4-phenyl-thiophen-2-yl)-3-oxo-propenyl]-benzaldehydeYield 31%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1-(5-ethyl-4-phenyl-thiophen-2-yl)-ethanone (600 mg, 2.61 mmol) and terephthalaldehyde (874 mg, 6.51 mmol) in ethanol (10 mL) and 5 N HCl in isopropanol (5 mL) is stirred at rt for 3 days. The reaction mixture is diluted with water and extracted with diethyl ether. The organic extract is washed with water and sat. aq. NaHCO3 solution and the solvent is evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 4-[3-(5-ethyl-4-phenyl-thiophen-2-yl)-3-oxo-propenyl]-benzaldehyde (280 mg) as a yellow solid, LC-MS: tR=1.14 min, [M+1]+=347.14, 1H NMR (CDCl3): δ 10.05 (s, 1H), 7.95-7.88 (m, 2H), 7.84-7.77 (m, 3H), 7.52-7.35 (m, 5H), 2.96 (q, J=7.6 Hz, 2H), 1.35 (t, J=7.6 Hz, 3H).

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe organic extract
  3. washis washed with water and sat. aq. NaHCO3 solution
  4. customthe solvent is evaporated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-47944dae2c8542a4a7d2a7914823adb8
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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