Réaction #6023

Équation de réaction

product

4-(bromomethyl)benzylalcohol

N,N-diisopropylethyl amine

t-butyldimethylsilyl chloride

→

title compound

Rendement 71.0%

4-(bromomethyl)-t-butyldimethylsilyloxymethylbenzene

Rendement 71.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   Lavagewashed with water, brine
4. 4
   Séchagedried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutreThe residue was chromatographed on silica (ethyl acetate/hexanes (2.5/97.5))

Mode opératoire

To a solution of the product of Example 4 Step A, (4.44 g, 22.1 mmol) in CH2Cl2 was added N,N-diisopropylethyl amine (1.2 eq.) and 4-dimethylaminopyridine (0.1 eq.), and t-butyldimethylsilyl chloride (1.2 eq.). The mixture was stirred for 1.5 hours at room temperature, then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water, brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was chromatographed on silica (ethyl acetate/hexanes (2.5/97.5)) to afford 5.0 g (71%) of the title compound.

Source