HCID 21883512, compound → HCID 21883544, compound

Participants

Reaction Steps

Ethyl-6-chloro-4-ethenyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylate (Example 142, Step 5)(0.433 g, 1.30 mmol) was dissolved in methanol (10 mL). Palladium (5 wt % on activated carbon)(0.150 g) was slowly added. The reaction vessel was charged with hydrogen 25 psi) and was stirred for 25 minutes. Gas chromatographic analysis indicated that the reaction was complete. The reaction mixture was filtered through Celite and evaporated to yield a orange oil. The oil was purified by flash column chromatography (100% hexanes) to yield the desired product as a yellow oil (0.282 g, 65%): 1H NMR (CDCl3 /300 MHz) 7.43 (d, 1H, J=2.4 Hz), 7.25 (dd, 1H, J=2.4, 8.7 Hz), 6.92(d, 1H, J=8.7 Hz), 5.75 (q, 1H, J=7.0 Hz), 4.38-4.24 (m, 2H), 3.05-2.95 (m, 2H), 1.35 (t, 3H, J=7.2 Hz), 1.25, (t, 3H, J=7.6 Hz).

Provenance & Evidence