Tetrahydrofuran → Cinnamoylbenzene

HRID 2095973Notes

Reaction equation

HRID 2095973 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=CS[C:16]=1C=O.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:16]=[CH:12][CH:11]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 68490alpha-HydroxyacetophenoneHCID 5813394-Methylthiazole-5-carboxaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 52%

Procedure

2.21 g (16.3 mmol) of 2-hydroxyacetophenone, 1.96 g of 4-methylthiazole-5-carboxaldehyde (7.86 mmol), and 10 ml of 25% NaOCH3 were reacted in 50 ml of dry THF to give 1.59 g (52%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.73 (s, 1H), 8.76 (s, 1H), 8.05 (d, d, J=0.9, 15.0 Hz, 1H), 7.82 (d, d, J=1.5, 8.1 Hz, 1H), 7.49 (d, d, d, J=1.5, 7.2, 8.4 Hz, 1H), 7.31 (d, J=15.0 Hz, 1H), 7.00 (d, d, J=0.9, 8.4 Hz, 1H), 6.95-6.93 (m, 1H), 2.62 (s, 3H).

Sources & evidence

ORD record
ord-0953ba8eea1245f3b8b4b02624c5e967
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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