Reaction #2487454

Reaction equation

t-butyldimethylsilyl trifluoromethanesulfonate

2,6-Lutidine

methylene chloride

benzyl 3-hydroxy-3-methylbutyrate

→

benzyl 3-(t-butyldimethylsilyloxy)-3-methylbutyrate

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Otherobtained in the step 1
2. 2
   Temperaturewith cooling with ice
3. 3
   workup.STIRRINGstirred for 1hour
4. 4
   Temperaturewith cooling on ice
5. 5
   OtherThe reaction liquid
6. 6
   Washwashed with water, aqueous saturated ammonium chloride solution and aqueous saturated sodium chloride solution
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated
9. 9
   Other4.5g of the residue was purified through silica gel column chromatography

Procedure

2,6-Lutidine (3.6g) was added to an anhydrous methylene chloride solution of benzyl 3-hydroxy-3-methylbutyrate (3.5g) obtained in the step 1, and stirred with cooling with ice. t-butyldimethylsilyl trifluoromethanesulfonate (3.9mL) was gradually added dropwise thereto, and stirred for 1hour with cooling on ice and then for 2hours at room temperature. The reaction liquid was diluted with ethyl acetate, then washed with water, aqueous saturated ammonium chloride solution and aqueous saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and concentrated. 4.5g of the residue was purified through silica gel column chromatography to give benzyl 3-(t-butyldimethylsilyloxy)-3-methylbutyrate (2.62g) as a colorless oil.

Source