Reaktion #164992

Reaktionsgleichung

1-bromo-4-butoxymethyl-benzene

n-butyl lithium

N,N-dimethylformamide

→

title compound

Ausbeute 81.3%

4-Butoxymethyl-benzaldehyde

Ausbeute 81.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat −78° C
2. 2
   TemperaturThis mixture was warmed to room temperature
3. 3
   workup.STIRRINGstirred for 20 minutes
4. 4
   SonstigeThe reaction solution was partitioned into water and ethyl acetate at 0° C
5. 5
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Sonstigethe solvent was evaporated under a reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1)

Vorschrift

To a solution of 1-bromo-4-butoxymethyl-benzene (11.5 g, 47.3 mmol) described in Manufacturing Example 4-1-1 in tetrahydrofuran (200 mL) was added n-butyl lithium (32.5 mL, 1.6 M hexane solution, 52.0 mmol) at −78° C. This mixture was stirred for 55 minutes at −78° C., and N,N-dimethylformamide (4.4 mL, 56.8 mmol) was added thereto at −78° C. This mixture was warmed to room temperature, and stirred for 20 minutes. The reaction solution was partitioned into water and ethyl acetate at 0° C. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (7.39 g, 81%).

Quelle