Reaktion #43996

Reaktionsgleichung

n-Butyl lithium

2-bromo-1,4-dimethoxy-3-methylnaphthalene

ethyl chloroformate

→

ethyl 1,4-dimethoxy-2-methylnaphthalene-3-carboxylate

Ausbeute 89.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched by addition of hydrochloric acid (2N)
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   TrocknenThe extract was dried (Na2SO4)
4. 4
   Sonstigethe solvent evaporated under vacuum
5. 5
   SonstigeThe residue was purified by SPE (silica, 10 g)
6. 6
   Wascheneluting with 10% ethyl acetate in cyclohexane

Vorschrift

n-Butyl lithium (1.6M in hexanes, 4.1 ml, 6.56 mmol) was added dropwise to 2-bromo-1,4-dimethoxy-3-methylnaphthalene (1.537 g, 5.47 mmol) in tetrahydrofuran (30 ml) at −50° C. The reaction was stirred for 30 min at −50° C. before dropwise addition of ethyl chloroformate (1 ml, 10.46 mmol). The reaction was allowed to warm to 0° C. over 18 h quenched by addition of hydrochloric acid (2N) and extracted with ethyl acetate. The extract was dried (Na2SO4) and the solvent evaporated under vacuum. The residue was purified by SPE (silica, 10 g) eluting with 10% ethyl acetate in cyclohexane to give ethyl 1,4-dimethoxy-2-methylnaphthalene-3-carboxylate (1.33 g, 89%).

Quelle