반응 #74633

반응 방정식

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

1-(diphenylmethyl)-3-hydrazinoazetidine dihydrochloride

→

title compound

수율 42.0%

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

수율 42.0%

용매

methyl-t-butyl ether

ethanol

acetic acid

반응 조건

후처리

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

실험 절차

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%.

출처