2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 68182961, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-4-(2-naphthyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide (0.235 g, 0.642 mmol) in THF (5.2 mL) at −78° C. was added 1.00 M Lithium hexamethyldisilazide in THF (0.771 mL, 0.771 mmol). The reaction mixture was stirred at −78° C. for 30 min, and [β-(trimethylsilyl)ethoxy]methyl chloride (0.341 mL, 1.93 mmol) was added at the same temperature. The mixture was stirred for 1 h at −78° C. and raised to rt. After stirring at rt for 30 min, the mixture was quenched by sat. NH4Cl, extracted with EA, dried and evaporated. The residue was purified by Isco silica gel chromatography (24 g cartridge), EA in hex, 0-30% using solid load to give the title compound (0.140 g, 42%). LCMS (FA) ES−: 494, 496. 1H NMR (400 MHz, DMSO) δ 7.95-7.92 (m, 4H), 7.55-7.52 (m, 2H), 7.32-7.29 (m, 1H), 6.77 (s, 1H), 6.74 (s, 1H), 4.91 (d, 1H), 4.64 (d, 1H), 4.20 (d, 1H), 3.95 (d, 1H), 3.52-3.47 (m, 2H), 0.85-0.76 (m, 2H), −0.05 (s, 9H).

Provenance & Evidence