Reaction #1753964

Reaction equation

(3-[1,3]dioxolan-2-ylphenyl)-phenyl-methanol

sodium iodide

dichloromethylsilane

→

title compound

3-Benzylbenzaldehyde

Solvents

acetonitrile

EtOAc

Conditions

Workup

1. 1
   Washwash with water, saturated sodium bicarbonate, 10% sodium thiosulfate
2. 2
   DryingDry the organic layers (Na2SO4)
3. 3
   Filtrationfilter
4. 4
   Concentrationconcentrate
5. 5
   Otherto give a residue
6. 6
   WashChromatograph the residue eluting with 9:1 hexane

Procedure

Combine (3-[1,3]dioxolan-2-ylphenyl)-phenyl-methanol (2.3 g, 8.7 mmol) and sodium iodide (5.3 g, 35.0 mmol) in acetonitrile (25 ml). Add dichloromethylsilane (2.1 ml, 17.4 mmol) via syringe. After 10 min, dilute with EtOAc and wash with water, saturated sodium bicarbonate, 10% sodium thiosulfate, and then brine. Dry the organic layers (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 9:1 hexane:EtOAc to give the title compound.

Source