反应详情

Isopropylmagnesium chloride-lithium chloride complex (2.98 ml, 3.88 mmol) was dissolved in THF (4 mL). Thiazole (0.252 ml, 3.52 mmol) in THF (2 mL) was added slowly. After 1 h, 1-(tert-butyldimethylsilyloxy)-2-propanone (0.816 ml, 423 mmol) in THF (2 mL) was added and the reaction was stirred for 3 h at room temperature. The reaction was quenched with saturated ammonium chloride and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification via silica gel column chromatography (5%-10% EtOAc:hexanes) afforded 1-{[tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-ol (383 mg, 40%) as a yellow oil. MS ESI: [M+H]+ m/z 274.

1. customThe reaction was quenched with saturated ammonium chloride
2. extractionextracted with EtOAc (3×)
3. dry with materialThe combined organics were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customPurification via silica gel column chromatography (5%-10% EtOAc:hexanes)