Reaction #49853

Reaction equation

alcohol

7-Hydroxymethyl-4-(3-thienyl)coumarin

hexamethylphosphorous triamide

CCl4

→

title compound

7--Chloromethyl-4-(3-thienyl)coumarin

Solvents

THF

Et2O

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Concentrationconcentrated
3. 3
   Otherthe residue chromatographed (30% EtOAc/hexane)

Procedure

To a solution of the alcohol from Step 1 (1.65 g) and hexamethylphosphorous triamide in 35 mL THF at 0° C. was added CCl4 (1.3 mL) and the mixture stirred for 30 min. The mixture was diluted with Et2O, filtered, concentrated and the residue chromatographed (30% EtOAc/hexane) to provide the title compound as a solid, m.p. 125°-127° C.

Source