Reaction #1459019

Reaction equation

n-butyllithium

hexane

benzaldehyde

2-(3-bromophenyl)-1,3-dioxolane

→

title compound

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

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.WAITAfter 1 hour
2. 2
   workup.WAITAfter 18 hours
3. 3
   Otherquench into water
4. 4
   Extractionextract with dichloromethane
5. 5
   Washwash sequentially with distilled water and brine
6. 6
   Dryingdry (Na2SO4)
7. 7
   Filtrationfilter
8. 8
   Concentrationconcentrate
9. 9
   Otherto give a residue
10. 10
    WashChromatograph the residue eluting with 7:3 hexane

Procedure

Combine 2-(3-bromophenyl)-1,3-dioxolane (10.0 ml, 66.0 mmol) and tetrahydrofuran (100 ml) and cool to about −78° C. Add dropwise a solution of n-butyllithium, 1.6 M solution in hexane (44.0 ml, 66.0 mmol). After 10 min, add a solution of benzaldehyde (7.6 ml, 66.0 mmol) in tetrahydrofuran (50 ml) via cannula. After 1 hour, warm to room temperature. After 18 hours, quench into 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