Reaktion #6023

Reaktionsgleichung

product

4-(bromomethyl)benzylalcohol

N,N-diisopropylethyl amine

t-butyldimethylsilyl chloride

→

title compound

Ausbeute 71.0%

4-(bromomethyl)-t-butyldimethylsilyloxymethylbenzene

Ausbeute 71.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle