Imidazole → 5-Bromomethyl-5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-1,3-dioxane

Temperature

25 °C

409 mg (1.71 mmol equivalents) of 5-bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane was dissolved in 5 mL of dimethylformamide, 233 mg (3.42 mmol equivalents) of imidazole and 309 mg (2.05 mmol equivalents) of t-butyldimethylchlorosilane were added thereto, and the mixture was stirred at room temperature (25° C.) for 18 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride and water were added thereto, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=20/1) to give 578 mg (1.64 mmol equivalents) of 5-bromomethyl-5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-1,3-dioxane.

1. customAfter completion of the reaction
2. extractionthe mixture was extracted three times with ethyl acetate
3. washThe combined ethyl acetate layers were washed with water and brine
4. dry with materialdried with anhydrous magnesium sulfate
5. concentrationsubsequently concentrated under vacuum
6. customthe obtained crude product
7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=20/1)

ORD record

ord-7510958ee0b04d159d72b74532efd04f

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09107964B2