Tetrahydrofuran → Cinnamoylbenzene

HRID 2095981Notes

Reaction equation

HRID 2095981 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]1N=C(C=O)S[CH:16]=1.O(C)[Na].[CH2:22]1[CH2:26]O[CH2:24][CH2:23]1>>[C:12]1([CH:11]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:16]=[CH:24][CH:23]=[CH:22][CH:26]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 68490alpha-HydroxyacetophenoneHCID 42634324-Methyl-1,3-thiazole-2-carbaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 17%

Procedure

2.27 g (16.7 mmol) of 2-hydroxyacetophenone, 2.0 g of 4-methylthiazole-2-carbaldehyde (15.7 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 0.67 g (17%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.67 (s, 1H), 7.98-7.95 (m, 1H), 7.80 (d, J=15.3 Hz, 1H), 7.89 (d, J=15.0 Hz, 1H), 7.53 (d, d, J=8.4, 8.4 Hz, 1H), 7.11 9s, 1H), 7.05 (d, J=8.4 Hz, 1H), 6.97 (d, d, J=7.5, 7.8 Hz, 1H), 2.56 (s, 3H).

Sources & evidence

ORD record
ord-eda83127d7604f92814c7eb60a09c50e
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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