Реакция #609124

Уравнение реакции

ammonium chloride

1-methyl-4-nitro-1H-pyrazole

(Z)-cyclohept-4-enone

lithium hexamethyldisilazide

→

(Z)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)cyclohept-4-enol

Выход 49.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураto warm to room temperature
2. 2
   Экстракцияextracted with EtOAc (150 mL)
3. 3
   ПромывкаThe organic layer was washed with water (30 mL)
4. 4
   Промывкаwashed with brine (20 mL)
5. 5
   Другоеseparated
6. 6
   Сушкаdried over MgSO4
7. 7
   Концентрированиеconcentrated under reduced pressure
8. 8
   ДругоеPurification via silica gel column chromatography (20-25% EtOAc)

Методика

To a solution of 1-methyl-4-nitro-1H-pyrazole (1.5 g, 11.8 mmol) and (Z)-cyclohept-4-enone (1.4 g, 13.0 mmol) in dry THF (30 mL) under nitrogen cooled to −78° C. was added dropwise a solution of lithium hexamethyldisilazide (1.0 M in THF, 30 mL, 29.5 mmol). The reaction mixture was allowed to warm to −40° C. and stirred for 90 min. Saturated aqueous ammonium chloride solution (30 mL) was added (dropwise initially) and the mixture was allowed to warm to room temperature and extracted with EtOAc (150 mL). The organic layer was washed with water (30 mL), washed with brine (20 mL), separated, dried over MgSO4 and concentrated under reduced pressure. Purification via silica gel column chromatography (20-25% EtOAc) gave (Z)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)cyclohept-4-enol as a tan oil (1.37 g, 49%).

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