Реакция #424787

Уравнение реакции

N-{2-[4-(hydroxymethyl)-2-naphthalenyl]ethyl}acetamide

sodium bicarbonate

→

title compound

N-[2-(4-Formyl-2-naphthalenyl)ethyl]acetamide

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added DMP (1.1 eq.) at 0° C
2. 2
   Другоеwas quenched with sat. aq. NaHSO3
3. 3
   Экстракцияextracted with Et2O
4. 4
   ПромывкаThe combined organic extracts were washed further with 10% aq. HCl, water and brine
5. 5
   Сушкаdried over Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеthe filtrate concentrated in vacuo
8. 8
   ДругоеPurification of the crude product
9. 9
   Другоеthus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Методика

To a suspension of N-{2-[4-(hydroxymethyl)-2-naphthalenyl]ethyl}acetamide (1 eq.) from the previous step and sodium bicarbonate (1.2 eq.) in dichloromethane (0.09 M) was added DMP (1.1 eq.) at 0° C. The resulting mixture was stirred at RT for 18 h before it was quenched with sat. aq. NaHSO3 and then extracted with Et2O. The combined organic extracts were washed further with 10% aq. HCl, water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

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