3,4,5-Trimethoxybenzaldehyde → 3-(2-Furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one

Temperature

-78 °C

2-Ethynylfuran (200 mg, 2.17 mmol) was dissolved in dry THF (10 ml) and cooled to −78° C. under N2 atmosphere. BuLi (1.2 ml, 2.4 mmol) was added slowly and stirred at −78° C. for 10 min and then 3,4,5-trimethoxybenzaldehyde (500 mg, 2.6 mmol) was added and reaction mixture was stirred for 1 h at −78° C. and then reaction temp raised to room temp. The reaction was quenched by addition of aqueous NH4Cl solution and extracted with EtOAc. The colorless oil was dissolved in dichloromethane and excess of MnO2 was added to it and stirred overnight at room temp. The reaction mixture was filtered through celite plug and evaporated to dryness. 3-(2-furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one was precipitated from ether by slow addition of hexane as off-white powder (65%). 1H NMR (300 MHz, CDCl3) δ 3.93 (s, 9H), 6.50-6.52 (m, 1H), 7.01 (d, J=3.6 Hz, 1H), 7.45 (s, 2H), 7.24 (s, 1H), 7.55 (d, J=1.5 Hz).

1. customreaction mixture
2. stirringwas stirred for 1 h at −78° C.
3. customreaction
4. temperaturetemp raised to room temp
5. customThe reaction was quenched by addition of aqueous NH4Cl solution
6. extractionextracted with EtOAc
7. dissolutionThe colorless oil was dissolved in dichloromethane and excess of MnO2
8. additionwas added to it
9. stirringstirred overnight at room temp
10. filtrationThe reaction mixture was filtered through celite plug
11. customevaporated to dryness
12. custom3-(2-furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one was precipitated from ether by slow addition of hexane as off-white powder (65%)

ORD record

ord-d4e7bfc35aae4c2e9f85151d0435d7ad

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278290B2