تفاعل #58912

معادلة التفاعل

hydrochloric acid

Sodium hydride

4-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde

ethyl diethylphosphonoacetate

→

(2E)-3-[4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-yl]acrylic acid

المردود 78.5%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with ethyl acetate
2. 2
   تركيزThe ethyl acetate layer was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in a mixture of 6N hydrochloric acid (18 ml) and acetic acid (2 ml)
4. 4
   workup.STIRRINGThe mixture was stirred for 1 hr
5. 5
   درجة الحرارةwith heating
6. 6
   درجة الحرارةunder reflux
7. 7
   تركيزThe reaction mixture was concentrated
8. 8
   workup.ADDITIONpoured into water
9. 9
   workup.ADDITION1N Sodium hydroxide was added for neutralization
10. 10
    ترشيحThe precipitated solids were collected by filtration
11. 11
    غسيلwashed with water
12. 12
    أخرىdried

الإجراء التجريبي

Sodium hydride (60% in oil, 60 mg) was added to a mixture of 4-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (168 mg), ethyl diethylphosphonoacetate (400 mg) and N,N-dimethylformamide (3 ml) at 0° C. and the mixture was stirred at room temperature for 15 min. The reaction mixture was poured into a 1N aqueous hydrochloric acid solution and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated and the residue was dissolved in a mixture of 6N hydrochloric acid (18 ml) and acetic acid (2 ml). The mixture was stirred for 1 hr. with heating under reflux. The reaction mixture was concentrated and poured into water. 1N Sodium hydroxide was added for neutralization. The precipitated solids were collected by filtration, washed with water, and dried to give (2E)-3-[4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-yl]acrylic acid (159 mg, 78%) as colorless crystals.

المصدر