Reaction #1459022

Reaction equation

(3-[1,3]-dioxolan-2-ylphenyl)phenylmethanol

(diethylamino)sulfur trifluoride

→

title compound

2-(3-(α-Fluorobenzyl)phenyl)-[1,3]-dioxolane

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherquench with water
2. 2
   Extractionextract with dichloromethane
3. 3
   Washwash sequentially with distilled water and brine
4. 4
   Dryingdry (Na2SO4)
5. 5
   Filtrationfilter
6. 6
   Concentrationconcentrate
7. 7
   Otherto give a residue
8. 8
   WashChromatograph the residue eluting with 7:3 hexane

Procedure

Combine (3-[1,3]-dioxolan-2-ylphenyl)phenylmethanol (2.3 g, 8.9 mmol) and dichloromethane (50 ml). Cool to about −78° C. Add dropwise a solution of (diethylamino)sulfur trifluoride (1.7 ml, 12.9 mmol). After 10 minutes, quench with water and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 7:3 hexane:EtOAc to give the title compound.

Source