Реакция #74633

Уравнение реакции

(2E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one

1-(diphenylmethyl)-3-hydrazinoazetidine dihydrochloride

→

title compound

Выход 42.0%

4-chloro-2-{1-[1-(diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}phenol

Выход 42.0%

Растворители

methyl-t-butyl ether

ethanol

acetic acid

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at 0° C. for 2 hours
2. 2
   ДругоеThe solvents were removed in vacuo
3. 3
   Другоеthe residue partitioned between ethyl acetate (80 ml) and saturated aqueous sodium hydrogencarbonate solution (50 ml)
4. 4
   ДругоеThe organic layer was separated
5. 5
   Сушкаdried over sodium sulphate
6. 6
   Фильтрацияfiltered
7. 7
   Другоеthe solvents removed in vacuo
8. 8
   Другоеto give a yellow gum
9. 9
   Другоеto crystallize

Методика

1-(diphenylmethyl)-3-hydrazinoazetidine dihydrochloride (Preparation 690, 1.00 g, 3.06 mmol) was added to an ice cold, stirred suspension of (2E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one (Preparation 759, 700 mg, 3.1 mmol) in ethanol (5 ml) and acetic acid (5 ml), stirred at 0° C. for 2 hours then allowed to warm up to room temperature over 2 hours. The solvents were removed in vacuo and the residue partitioned between ethyl acetate (80 ml) and saturated aqueous sodium hydrogencarbonate solution (50 ml). The organic layer was separated and dried over sodium sulphate, filtered and the solvents removed in vacuo to give a yellow gum. This was dissolved in warm methyl-t-butyl ether (20 ml) and allowed to crystallize to give the title compound as a pale yellow powder, 541 mg, yield 42%.

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