Реакция #2334

Уравнение реакции

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

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe DMF was evaporated in vacuo
2. 2
   Другоеthe residue partitioned between dichloromethane and water
3. 3
   ЭкстракцияThe aqueous phase was extracted with further dichloromethane
4. 4
   ПромывкаThe combined organic extracts were washed with water
5. 5
   Другоеthen dried
6. 6
   Другоеevaporated
7. 7
   ДругоеThe residue was purified by chromatography on alumina
8. 8
   Промывкаeluting with dichloromethane
9. 9
   ДругоеEvaporation of the appropriate fractions

Методика

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)+.

Источник