Reaktion #1361398

Reaktionsgleichung

n-butyllithium

hexane

benzaldehyde

ethyl acetate

→

desired product

Ausbeute 51.0%

m-(1,3-Dioxolan-2-yl)-benzhydrol

Ausbeute 51.0%

Lösungsmittel

tetrahydofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe solution left
2. 2
   workup.STIRRINGto stir for 1 hour
3. 3
   Waschenwashed with water
4. 4
   TrocknenThe organic layer was dried (MgSO4)
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto afford an oil which
7. 7
   Sonstigewas chromatographed on silica gel
8. 8
   WaschenElution with ethyl acetate/hexane (1:2)

Vorschrift

A stirred solution of the acetal (1.0 g, 4.37 mmol) of Description 1 in dry tetrahydrofuran (50 ml), under argon, was cooled to -80° and treated with a 1.6 M solution of n-butyllithium in hexane (2.73 ml, 4.37 mmol). The resulting yellow solution was stirred at -80° for 0.5 hours. A solution of redistilled benzaldehyde (0.44 ml, 4.37 mmol) in dry tetrahydofuran (5 ml) was added over 2 minutes and the solution left to stir for 1 hour. The reaction mixture was warmed to room temperature over the next hour and then diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4) and evaporated to afford an oil which was chromatographed on silica gel. Elution with ethyl acetate/hexane (1:2) gave the desired product as a colourless oil (0.57 g, 51%). δH (CDCl3) 2.23 (1H, d, J 3.5 Hz), 4.1 (4H, m), 5.80 (1H, s), 5.87 (1H, d, J 3.5 Hz), 7.2-7.6 (9H) ppm. EIMS M+ 256.

Quelle