Ethyl Acetate → HCID 59350828, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of lithium aluminum hydride (399 mg, 10.5 mmol) in tetrahydrofuran (25 mL) was cooled to 0° C. under a stream of argon. A solution of 4-(4-ethanesulfonyl-benzyl)-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (870 mg, 2.18 mmol) in tetrahydrofuran (30 mL) was added slowly drop-wise to the 0° C. suspension. The reaction mixture was stirred at 0° C. for 15 minutes. The reaction mixture was warmed to room temperature and it was stirred at room temperature for 15 minutes. The reaction mixture was cooled again to 0° C. Ethyl acetate was added drop-wise to quench the unreacted lithium aluminum hydride. A saturated aqueous solution of potassium sodium tartrate was added. The organic phase was separated, dried over MgSO4, filtered, and concentrated to afford 780 mg (96%) of [4-(4-ethanesulfonyl-benzyl)-6-fluoro-3-methyl-naphthalen-2-yl]-methanol as an oily white solid. This product was used in subsequent reactions without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.98 (dd, J=8.9, 6.2 Hz, 1 H), 7.90 (s, 1 H), 7.73 (d, J=8.2 Hz, 2 H), 7.67 (d, J=12.4 Hz, 1 H), 7.34 (dd, J=8.9, 2.1 Hz, 1 H), 7.29 (d, J=8.2 Hz, 2 H), 5.27 (t, J=5.1 Hz, 1 H), 4.66 (d, J=5.1 Hz, 2 H), 4.58 (s, 2 H), 3.20 (q, J=7.2 Hz, 2 H), 2.31 (s, 3 H), 1.04 (t, J=7.2 Hz, 3 H). HRMS (ES+) cald. for C21H21FO3S [(M+Na)+] 395.1087, obsd. 395.1088.

Provenance & Evidence