Tetrahydrofuran → Cinnamoylbenzene

HRID 2095975Notes

Reaction equation

HRID 2095975 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][C:12]1ON=C(C=O)[CH:13]=1.O(C)[Na].[CH2:22]1[CH2:26]O[CH2:24][CH2:23]1>>[C:22]1([CH:26]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:13]=[CH:12][CH:11]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 68490alpha-HydroxyacetophenoneHCID 27952225-Methyl-1,2-oxazole-3-carbaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 29%

Procedure

2.24 g (16.5 mmol) of 2-hydroxyacetophenone, 1.65 g of 5-methylisoxazole-3-carbaldehyde (14.9 mmol), and 10 ml of 25% NaOCH3 were reacted in 50 ml of dry THF to give 1.59 g (29%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.53 (s, 1H), 7.87 (d, d, J=0.6, 7.5 Hz, 1H), 7.80 (d, J=15.6 Hz, 1H), 7.69 (d, J=15.6 Hz, 1H), 7.56-7.51 (m, 1H), 7.05 (d, d, J=0.6, 8.4 Hz, 1H), 6.99-6.93 (m, 11H), 6.31 (d, J=0.3 Hz, 1H), 2.50 (s, 3H).

Sources & evidence

ORD record
ord-11c227b382d74c3188ff322d69195c38
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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