Reaktion #2267744

Reaktionsgleichung

N,N-dimethylformamide

6-bromo-4-tert-butyl-7-ethoxy-1,1-dimethyl-1,2-dihydronaphthalene

n-butyllithium

→

title compound

8-tert-Butyl-3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalene-2-carbaldehyde

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe reaction mixture was quenched with water
3. 3
   Extraktionextracted with ether
4. 4
   WaschenThe combined organic layers were washed with water and brine
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigePurification by flash column chromatography (silica gel, 3% to 10% ethyl acetate in hexane)

Vorschrift

To a solution of 6-bromo-4-tert-butyl-7-ethoxy-1,1-dimethyl-1,2-dihydronaphthalene (Compound A-6, 600 mg, 1.78 mmol) in ether (10 mL) at −78° C. was added n-butyllithium (2.3 mL 1.6 M in hexane, 3.9 mmol). After stirring at −78° C. for 25 nm, N,N-dimethylformamide (2 mL) was added and the reaction mixture was allowed to warm to −40° C. over 10 min. The reaction mixture was quenched with water and extracted with ether. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 3% to 10% ethyl acetate in hexane) afforded the title compound as a white solid.

Quelle