Реакция #41551

Уравнение реакции

sodium bicarbonate

diisopropylamine

triphenyl phosphine

2-phenyl-ethanol

1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)pyrrolidin-1-yl)-ethanone

1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

diisopropylamine

triphenyl phosphine

2-phenyl-ethanol

→

1-(2-(6-phenethyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe reaction liquid
2. 2
   Другоеthe reaction liquid
3. 3
   workup.STIRRINGwas stirred overnight at room temperature
4. 4
   Экстракцияthis was extracted with ethyl acetate
5. 5
   Сушкаdried with anhydrous magnesium sulfate
6. 6
   ДругоеThe solvent was evaporated away under reduced pressure
7. 7
   Другоеthe resulting residue was purified
8. 8
   Другоеthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate)
9. 9
   Другоеto obtain the entitled compound as a brown oily substance

Методика

0.019 ml of diisopropylamine, 27.6 mg of triphenyl phosphine and 0.011 ml of 2-phenyl-ethanol were added in order to a tetrahydrofuran (1 ml) solution of 29.2 mg of 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)pyrrolidin-1-yl)-ethanone obtained in Example 121 (step 10), and the reaction liquid was stirred for 6 hours at room temperature. 0.040 ml of diisopropylamine, 53.2 mg of triphenyl phosphine and 0.023 ml of 2-phenyl-ethanol were added in order to the reaction liquid, and the reaction liquid was stirred overnight at room temperature. Aqueous saturated sodium bicarbonate was added to the reaction liquid, and this was extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate) to obtain the entitled compound as a brown oily substance.

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