反应详情

Under nitrogen, a stirred solution of 79 mg (0.24 mmol) of 1-[2-(4-hydroxymethylphenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene (Example 9) in 2 mL of dry THF at 0° C. was treated with 15 mg (0.6 mmol) off sodium hydride (95%); after 30 minutes, 0.1 mL (1.6 mmol) of methyl iodide was added and the reaction was allowed to warm to ambient temperature overnight. The solvent was removed in in vacuo; the residue was dissolved in ethyl acetate and washed with water, dried (MgSO4), and reconcentrated. Purification by silica gel chromatography (MPLC) with hexane/ethyl acetate (5:1) and subsequent lyophilization from acetonitrile/water (1:1) gave 25 mg (30%) of 1-[2-(4-methoxymethyl phenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene as a colorless solid: NMR (CDCl3) d 2.09 (m, J=7 Hz, 2H), 2.92 (t, J=7 Hz, 4H), 3.03 (s, 3H), 3.40 (s, 3H), 4.42 (s, 2H), 7.12 (d, J=8 Hz, 2H), 7.20 (d, J=8 Hz, 2H), 7.33 (d, J=8 Hz, 2H), 7.73 (d, J=8 Hz, 2H; MS (EI) m/e (rel intensity) 342 (100), 81 (27), 69 (62). HRMS. Calc'd for C20H22O3S: 342.1290. Found: 342.13 01. Anal. Calc'd for C20H22O3S: C, 70.15; H, 6.48; S, 9.3 6. Found: C, 69.86; H, 6.64; S, 9.38.

1. customThe solvent was removed in in vacuo
2. dissolutionthe residue was dissolved in ethyl acetate
3. washwashed with water
4. dry with materialdried (MgSO4)
5. customPurification by silica gel chromatography (MPLC) with hexane/ethyl acetate (5:1) and subsequent lyophilization from acetonitrile/water (1:1)