Trifluoromethanesulfonate → HCID 58703563, compound

Participants

Reaction Conditions

Reaction Steps

Purge a solution of 1-bromo-2,5-bis-methoxymethoxy-3-methoxymethyl-benzene (2.76 g, 8.59 mmol) in THF (17 mL) with nitrogen and cool to −70° C. Clowly add a solution of phenyllithium (4.3 mL of a 2.0 M solution in dibutyl ether, 8.59 mmol) to the cooled solution, keeping the temperature below −60° C. After 35 minutes, add a solution of ZnCl2 (8.6 mL of a 1.0 M solution in Et2O, 8.59 mmol) and warm the reaction to 0° C. Purge a solution of 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid methyl ester (2.36 g, 8.59 mmol) in THF (17 mL) with nitrogen. To the cooled zincate solution, add Pd(PPh3)4 (0.496 g, 0.430 mmol) followed by the triflate solution. Heat this mixture to 50° C. overnight then cool to room temperature. Quench the reaction with H2O and extract with EtOAc (3×50 mL). Combine the organic extracts, dry (Na2SO4), filter and concentrate. Purify the crude material using silica gel chromatography eluting with Hex:EtOAc (75:25, then 50:50) to afford the subtitled product (1.76 g, 56%) as an oil. 1H NMR (CDCl3) δ 1.95-2.05 (m, 2H), 2.78-2.85 (m, 4H), 3.42 (s, 3H), 3.47 (s, 6H), 3.57 (s, 3H), 4.51 (s, 2H), 4.80 (s, 2H), 5.12 (s, 2H), 6.74 (d, J=3.1 Hz, 1H), 7.04 (d, J=3.1 Hz, 1H).

Provenance & Evidence