Water → HCID 15589953, compound

Participants

Reaction Steps

A mixture of 3.8 g (17.2 mmol) of 1-(5-carbethoxythien-2-yl)-2-methyl-1-propene and 5.0 g (45 mmol) of SeO2 in 60 mL of dioxane and 0.8 mL (44 mmol) of H2O was degassed three times under argon and heated under reflux for 45 min. Cooling, filtration over Celite, and concentration gave 6.8 g of a light-brown solid, which was diluted with 50 mL of Et2O and filtered. The filtrate was concentrated and passed over a column of 150 g of silica gel (15% EtOAc/hexane) to give 2.35 g (60% yield) of the aldehyde as a pale yellow solid, a portion of which was recrystallized from EtOAc/hexane to give white needles, mp 98° C: IR (mull) 1720, 1680, 1620, 1380, 1290, 1250, 1180, 1160, 1100, 1020, 890, 850, 815, 750 cm-1 ; 1H NMR (CDCl3) δ1.42 (t, J=7 Hz, 3, CH2CH3), 2.17 (s, 3, C=CCH3), 4.47 (q, J=7 Hz, 2, CH2CH3), 7.40 (d, J=4 Hz, 1, 3' C=CH), 7.43 (s, 1, C=CH), 7.83 (d, J=4 Hz, 1, 4' C=CH), 9.63 (s, 1, CHO); MS calcd for C11H12O3S 224.0507, found 224.0519.

Provenance & Evidence