3-Pyridinecarboxaldehyde → Cinnamoylbenzene

HRID 1019448Notes

Reaction equation

HRID 1019448 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][CH:14]=[C:13]([CH:17]=O)[CH:12]=1.O([CH3:21])[Na]>C1COCC1>[C:13]1([CH:17]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:14]=[CH:15][CH:16]=[CH:21][CH:12]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 68490alpha-HydroxyacetophenoneHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.36 g (17.3 mmol) of 2-hydroxyacetophenone, 1.7 g of 3-pyridine-carboxaldehyde (15.9 mmol), and 9 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 2.05 g (57%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.66 (s, 1H), 8.93 (d, J=1.8 Hz, 1H), 8.67 (d, d, J=1.5, 4.8 Hz, 1H), 8.03-8.00 (m, 1H), 7.92 (d, J=15.7 Hz, 1H), 7.91 (d, J=1.5 Hz, 1H), 7.76 (d, J=15.6 Hz, 1H), 7.58-7.52 (m, 1H), 7.43 (d, d, J=5.1, 8.1 Hz, 1H), 7.07 (d, d, J=0.9, 8.1 Hz, 1H), 6.99 (d, d, d, J=1.2, 7.2, 8.1 Hz, 1H).

Sources & evidence

ORD record
ord-3e640bf3e656438fb9d5d66a93dd2a8e
Source dataset
uspto-grants-2014_05
Patent number
US08715761B2

Reaction notes

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