Reaktion #1459019

Reaktionsgleichung

n-butyllithium

hexane

benzaldehyde

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

→

title compound

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

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 1 hour
2. 2
   workup.WAITAfter 18 hours
3. 3
   Sonstigequench into water
4. 4
   Extraktionextract with dichloromethane
5. 5
   Waschenwash sequentially with distilled water and brine
6. 6
   Trocknendry (Na2SO4)
7. 7
   Filtrationfilter
8. 8
   Einengenconcentrate
9. 9
   Sonstigeto give a residue
10. 10
    WaschenChromatograph the residue eluting with 7:3 hexane

Vorschrift

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.

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