Реакция #1181094

Уравнение реакции

cyclobutanone

BF3

NH4Cl

butyllithium

ethyl [(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]acetate

hexamethyldisilazane

→

Ethyl(1-hydroxycyclobutyl)-[(3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]-acetate

Растворители

THF

hexane

THF

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   workup.STIRRINGthe mixture was stirred at −78° C. for 2 h, at −50° C. for 1 h and at 0° C. for 1 h
4. 4
   workup.STIRRINGthe mixture was stirred for 30 min
5. 5
   ДругоеThe organic phase was separated off
6. 6
   Другоеthe solvents were removed under reduced pressure
7. 7
   ДругоеThis gave 9.88 g (100%) of colorless crystals which were reacted without further purification

Методика

23.0 ml of hexamethyldisilazane (mmol) were dissolved in 200 ml of THF, and 46 ml of 2.5M (115 mmol) of butyllithium solution in hexane were added dropwise at −78° C. After 30 min, 7.90 g (22.3 mmol) of ethyl [(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]acetate, dissolved in 50 ml of THF, were added dropwise, and the mixture was stirred at −78° C. for 1.5 h. 3.0 g (42.8 mmol) of cyclobutanone and 4.14 g (29.2 mmol) of BF3-etherate, dissolved in 50 ml of THF, were added dropwise, and the mixture was stirred at −78° C. for 2 h, at −50° C. for 1 h and at 0° C. for 1 h. 100 ml of saturated NH4Cl solution were added dropwise, and the mixture was stirred for 30 min. The organic phase was separated off and the solvents were removed under reduced pressure. This gave 9.88 g (100%) of colorless crystals which were reacted without further purification.

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