反应详情

A stirred suspension of 3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.15 g, 0.68 mmol) in THF (5 mL) was treated with NaH (0.032 g, 60% dispersion in oil, 0.81 mmol) at r.t. After 5 minutes [2-(chloromethoxy)ethyl]-trimethylsilane (0.14 mL, 0.81 mmol) was added and the reaction mixture stirred for 1.5 h. The reaction mixture was quenched with water (5 mL), diluted with EtOAc (20 mL) and the organic fraction separated. The organic fraction was dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 0-40% EtOAc/hexanes) gave the title compound (0.206 g, 86%) as a clear oil. δH (CDCl3) 5.35 (2H, s), 3.60 (2H, m), 2.50 (3H, s), 2.35 (3H, s), 1.35 (12H, s), 0.90 (2H, m), 0.00 (9H, s). LCMS (ES+) 353.0 (M+H)+.

1. customThe reaction mixture was quenched with water (5 mL)
2. additiondiluted with EtOAc (20 mL)
3. customthe organic fraction separated
4. dry with materialThe organic fraction was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customPurification by column chromatography (SiO2, 0-40% EtOAc/hexanes)