تفاعل #43996

معادلة التفاعل

n-Butyl lithium

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

ethyl chloroformate

→

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

المردود 89.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched by addition of hydrochloric acid (2N)
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   تجفيفThe extract was dried (Na2SO4)
4. 4
   أخرىthe solvent evaporated under vacuum
5. 5
   أخرىThe residue was purified by SPE (silica, 10 g)
6. 6
   غسيلeluting with 10% ethyl acetate in cyclohexane

الإجراء التجريبي

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%).

المصدر