تفاعل #353940

معادلة التفاعل

Sodium hydride

product

4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenol

ethyl 6-bromohexanoate

→

ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe DMF was evaporated in vacuo
2. 2
   أخرىthe residue partitioned between dichloromethane and water
3. 3
   استخلاصThe aqueous phase was extracted with further dichloromethane
4. 4
   غسيلThe combined organic extracts were washed with water
5. 5
   أخرىthen dried
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue was purified by chromatography on alumina
8. 8
   غسيلeluting with dichloromethane
9. 9
   أخرىEvaporation of the appropriate fractions

الإجراء التجريبي

Sodium hydride (50% w/w dispersion in mineral oil, 55 mg) was added under argon to a stirred solution of the product from step (iii) above (300 mg) in dry DMF (5 ml). After five minutes, ethyl 6-bromohexanoate (0.20 ml) was added and the mixture stirred for 16 hours. The DMF was evaporated in vacuo and the residue partitioned between dichloromethane and water. The aqueous phase was extracted with further dichloromethane. The combined organic extracts were washed with water then dried, and evaporated. The residue was purified by chromatography on alumina, eluting with dichloromethane and then 1% v/v methanol/dichloromethane. Evaporation of the appropriate fractions gave ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate, 260 mg, as a yellow gum: NMR (CDCl3) δ 8.40 (2H, dd), 7.16 (2H, dd), 7.07 (2H, m), 6.90 (2H, m), 4.13 (2H, q), 3.98 (2H, t), 2.34 (2H, t), 1.78 (4H, m), 1.57 (2H, m), 1.44 (9H, s), 1.26 (3H, t); m/e 429 (M+H)+.

المصدر