2,4,6-Trimethylpyridine → 3-(t-Butyldiphenylsiloxymethy)benzyl chloride

Participants

Reaction Steps

Methanesulfonyl chloride (3.96 g, 34.6 mmol) was added dropwise to a stirred solution of 23 (11.8 g, 31.4 mmol), LiCl (1.33 g, 31.4 mmol), and s-collidine (4.19 g, 34.6 mmol) in anhydrous DMF (120 mL) at 0° C. under argon. The reaction mixture was allowed to warm to room temperature over 2 h, and was then poured into water and extracted twice with diethyl ether. The organic layers were combined and washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 11.8 g (95%) of 24 as a clear, dark yellow liquid. The chloride was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3) δ7.72-7.76 (m, 4H, ArH), 7.31-7.48 (m, 10H, ArH), 4.82 (s, 2H, CH2OSi), 4.62 (s, 2H, CH2C1), and 1.15 (s, 9H, SiC(CH3)3); 13C NMR (75 MHz, CDCl3) δ141.71, 137.35, 135.58, 135.51, 133.39, 129.74, 129.60, 128.64, 127.74, 127.08, 126.20, 126.06, 65.24 (CH2OSi), 46.34 (CH2C1), 26.84 (SiC(CH3)3), and 19.32 (SiC(CH3)3); MS (DCI) m/e 395 (MH+).

Provenance & Evidence