(Diethylamino)sulfur trifluoride → 2-(3-(alpha-Fluorobenzyl)phenyl)-[1,3]-dioxolane
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)O)[CH:9]=[CH:10][CH:11]=1.C(N(S(F)(F)[F:26])CC)C>ClCCl>[F:26][CH:12]([C:8]1[CH:7]=[C:6]([CH:2]2[O:3][CH2:4][CH2:5][O:1]2)[CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
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.