Dimethylformamide → HCID 18549152, compound

Participants

Reaction Steps

Using an analogous formylation procedure to that employed by Campaigne et al 3-ethoxycumene (5 g, 30.49 mmol) was added dropwise to a mixture of phosphorous oxychloride (2.84 mL, 30.5 mmol) and DMF (8.6 mL, 0.111 mol) at 0° C. and the resultant mixture was heated to 80-90° C. for 48 hrs before being poured onto crushed ice. The solution was taken to pH 7 with saturated sodium acetate, extracted with diethyl ether and upon drying and solvent removal a clear colourless oil was obtained. Column chromatography (silica, ethyl acetate/hexane, 1:9, Rf 0.44) gave the title compound as a clear colourless oil (202.4 mg, 7.5% based on reacted material). 1H n.m.r. [400 MHZ, CDCl3] δ 10.11, S, 1H, CHO; 7.715, d, J 8.8 Hz, 1H, H6; 6.865, d, J 2.4 Hz, 1H, H3; 6.75, dd, J 8.55, 2.4 Hz, 1H, H5; 4.05, q, J 7 Hz, 2H, CH2; 3.95, septet, J 6.9 Hz, 1H, CH(CH3)2; 1.39, t, J 7 Hz, 3H, CH3; 1.225, d, J 7.1, 6H, CH(CH3)2. 13C n.m.r. [100 MHZ, CDCl3] δ 190.53, CHO; 163.42, C4; 153.87, C2; 134.77, C6; 126.37, C1, 112.42, C3; 110.87, C5; 63.48, OCH2CH3; 27.52, CH(CH3)2; 23.48, CH(CH3)2; 14.47, OCH2CH3. Mass spectrum (f.a.b.) calculated 192.115023, found 192.1151.

Provenance & Evidence