2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(Benzofuran-5-yl)propan-1-one
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-(2,3-dihydrobenzofuran-5-yl)propan-1-one (40 g, 1.0 eq) and 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (62 g, 1.2 eq) in 400 mL anhydrous 1,4-dioxane was refluxed overnight, cooled, quenched with sat NaHCO3 (aq), and extracted with EtOAc. The extract was washed with brine, dried, concentrated, and purified by column chromatography to give the desired product (10.3 g, 26%). 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=2.0 Hz, 1H), 7.98 (dd, J=8.8 Hz, 2.0 Hz, 1H), 7.69 (d, J=2.0 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 6.86 (d, J=2.0 Hz, 1H), 3.07 (q, J=7.2 Hz, 2H), 1.26 (t, J=7.2 Hz, 3H).