Hydrochloric Acid → HCID 58935008, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21a, Step 2 (2.41 g, 5.00 mmole), n-buytylvinyl ether (3.22 mL, 25.0 mmole), Pd(OAc)2 (33.4 mg, 0.150 mmole), DPPP (136 mg, 0.330 mmole) and K2CO3 (0.830 g, 6.00 mmole), in a mixture of DMF (12.5 mL) and H2O (1.5 mL) was stirred at 100° C. for 17 hrs. After the mixture was cooled to room temperature, 1N HCl (20 mL) was then added and the mixture was stirred for 30 minutes and then was extracted with EtOAc (2×200 mL). The extracts were combined and washed with H2O (200 mL), brine (100 mL), dried over MgSO4, and filtered. The solvent was removed in vacuo to give the crude product as a dark brown oil. Purification by silica chromatography (20% EtOAc in hexanes with 1% HOAc) gave 0.940 g (47% yield) of the product as a tan crystalline solid: EIHRMS m/z 370.0258 (M+, C14H8F6O5, Calc'd 370.0276). 1H NMR (dmso-d6/300 MHz) 13.59 (brs, 1H), 7.95 (s, 1H), 7.85 (d, 1H, J=2.8 Hz), 7.58 (dd, 1H, J=4.0, 2.2 Hz), 6.19 (q, 1H, J=7.0 Hz), 2.58 (s, 3H).

Provenance & Evidence