Reaction #1586

Reaction equation

Raloxifene HCl

triethylamine

linolenoyl chloride

→

Raloxifene

Solvents

THF

Conditions

Workup

1. 1
   OtherThis derivative was prepared in a manner similar to Example 1
2. 2
   OtherThe final product was chromatographed on a silica gel column
3. 3
   Washeluted with EtOAc-hexane (8:2)

Procedure

This derivative was prepared in a manner similar to Example 1, using 2.6 g (0.005 mol) of Raloxifene HCl, 2 g (0.02 mol) of triethylamine, 20 mg of DMAP, and 3.2 g (0.01 mol) of linolenoyl chloride in 250 mL of THF. The final product was chromatographed on a silica gel column eluted with EtOAc-hexane (8:2). This yielded 3.21 g of the title compound as clear oil.

Source