2-Pyridinecarboxaldehyde → Cinnamoylbenzene

HRID 2095982Notes

Reaction equation

HRID 2095982 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]=[CH:13][C:12]=1[CH:17]=O.O([CH3:21])[Na]>C1COCC1>[C:12]1([CH:17]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:21]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 68490alpha-HydroxyacetophenoneHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.08 g (15.3 mmol) of 2-hydroxyacetophenone, 1.55 g of 2-pyridine-carboxaldehyde (14.5 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 1.4 g (43%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.76 (s, 1H), 8.73 (d, J=4.5 Hz, 1H), 8.29 (d, J=15.3 Hz, 1H), 8.06 (d, d, J=1.5, 8.1 Hz, 1H), 7.78 (d, J=15.0 Hz, 1H), 7.77 (d, d, d, J=1.8, 7.5, 9.3, 1H), 7.56-7.50 (m, 2H), 7.37-7.32 (m, 1H), 7.05 (d, J=8.4 Hz, 1H), 7.01-6.94 (m, 1H).

Sources & evidence

ORD record
ord-796c1f2cf93d46ef8853b56f9d2e0980
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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