4-Pyridinecarboxaldehyde → Cinnamoylbenzene

HRID 2095983Notes

Reaction equation

HRID 2095983 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].N1[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=1.O([CH3:21])[Na]>C1COCC1>[C:14]1([CH:17]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:15]=[CH:16][CH:21]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 68490alpha-HydroxyacetophenoneHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.26 g (16.6 mmol) of 2-hydroxyacetophenone, 1.68 g of 4-pyridine-carboxaldehyde (15.7 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 1.02 g (29%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.56 (s, 1H), 8.72-8.70 (m, 2H), 7.90 (d, d, J=1.5, 7.8 Hz, 1H), 7.80 (s, 2H), 7.56-7.48 (m, 3H), 7.05 (d, d, J=0.9, 8.4 Hz, 1H), 6.97 (d, d, J=7.2, 7.5 Hz, 1H).

Sources & evidence

ORD record
ord-4d3aa58aa02b4c78a206eeeedef4a838
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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