Methoxytrimethylsilane → HCID 66696670, compound

Participants

Reaction Steps

A solution of Example 52B (1.26 g, 5.22 mmol) in CH2Cl2 (5 mL) was cooled to −78° C. after which the starting material was observed to precipitate. Methoxytrimethylsilane (1.44 mL, 10.5 mmol) and trimethylsilyltrifluoromethane sulfonate (0.047 mL, 0.261 mmol) were added and the reaction mixture was allowed to proceed for 24 hr with gradual warming to ambient temperature. The reaction was quenched with saturated aq NaHCO3 solution (10 mL), then diluted with EtOAc (50 mL) and H2O (30 mL). The separated aqueous phase was extracted with EtOAc, and the combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The result was 1.42 g (95%) of the title compound as a yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1H), 7.98 (d, J=8.7, 2H), 7.87 (d, J=8.4, 2H), 5.55 (s, 1H), 3.34 (s, 6H). MS (DCI+) m/z 288 (M+H).

Provenance & Evidence