Sodium Iodide → 3-Benzyl-6-cyclopentyl-6-[2-(4-methoxyphenyl)ethyl]tetrahydropyran-2,4-dione

Participants

Reaction Steps

DBU (28.6 ul, 0.191 mmol) was added to a solution of 6-cyclopentyl-6-[2-(4-methoxyphenyl)ethyl]dihydro-2H-pyran-2,4(3H)-dione (55 mg, 0.174 mmol, described below) in benzene (1.9 ml), under an atmosphere of argon. Benzyl bromide (21 ul, 0.174 mmol) was then added. The reaction mixture was stirred at room temperature for 20 minutes, followed by the addition of 5 crystals of sodium iodide. The reaction mixture was stirred for a further 24 hrs, after which time the mixture was filtered through a plug of Celite. The filtrate was concentrated in vacuo and the residue purified by prep HPLC to afford the title compound as a white solid (9.0 mg). 1H NMR (CDCl3): δ 1.43-1.80 (bm, 8H), 2.20 (m, 2H), 2.24 (m, 1H), 2.72 (m, 2H), 3.06 (m, 3H), 3.30 (m, 1H), 3.76 (m, 4H), 6.72 (d, J=8.64 Hz, 2H), 6.78 (d, J=8.64 Hz, 2H), 6.94 (m, 3H), 7.23 (m, 2H). Exact Mass: Calcd, 406.51; Found, 406.21.

Provenance & Evidence