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 (9.64 g, 20.0 mmole), n-buytylvinyl ether (12.9 mL, 100 mmole), Pd(OAc)2 (135 mg, 0.600 mmole), DPPP (544 mg, 1.32 mmole) and K2CO3 (3.32 g, 24.0 mmole), in a mixture of DMF (50 mL) and H2O (6 mL) was stirred at 100° C. for 46 hrs. After the mixture was cooled to room temperature, 1N HCl (100 mL) was then added and the mixture 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 and the crude product was purified by silica chromatography (20% EtOAc in hexanes with 1% HOAc) to give 2.12 g (29% yield) of 8-acetyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid prepared as in Example 21b as well as 1.44 g (18% yield) of the title compound as a yellow crystalline solid: ESHRMS m/z 399.0654 (M+H, C16H13F6O5, Calc'd 399.0662).

Provenance & Evidence