反应详情

To a solution of cis-3-benzyloxymethylcyclobutanol (Albany Molecular Research Institute, 1.0 g, 5.2 mmol) in 50 mL of CH2Cl2 was added imidazole (2.7 g, 39 mmol) followed by tert-butyldimethylsilyl chloride (3.9 g, 26 mmol). This mixture stirred at ambient temperature for 2 hours and was quenched with 10 mL of saturated aqueous NH4Cl. The layers were separated and the aqueous layer was extracted with three 5 mL of portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 75% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 307 (M+H)+.

1. customwas quenched with 10 mL of saturated aqueous NH4Cl
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with three 5 mL of portions of CH2Cl2
4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customPurification via column chromatography (SiO2, 75% hexanes in ethyl acetate)