تفاعل #51990

معادلة التفاعل

3-pyridinecarboxaldehyde

trimethylsulfonium methylsulfate

NaOH

→

title compound

المردود 28.6%

3-Oxiran-2-ylpyridine

المردود 28.6%

المذيبات

CH2Cl2

H2O

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGwhile stirring
2. 2
   درجة الحرارةthe mixture subsequently refluxed for 1 h
3. 3
   درجة الحرارةAfter cooling to room temperature
4. 4
   ترشيحthe mixture is filtered
5. 5
   استخلاصthe filtrate extracted with CH2Cl2
6. 6
   تجفيفThe combined extracts are dried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىto yield a red oil, which
10. 10
    workup.DISTILLATIONis subjected to Kugelrohr distillation under high vacuum at 150° C.

الإجراء التجريبي

To a solution of 2.59 g of 3-pyridinecarboxaldehyde and 62 mg of tetra-n-butylammonium bromide in 60 mL CH2Cl2 at room temperature is added a solution of 10.0 g of trimethylsulfonium methylsulfate in 15 mL H2O. The resulting solution is set stirring and cooled to 0° C. Aqueous NaOH (50% w/w; 40 mL) is added in portions while stirring and the mixture subsequently refluxed for 1 h. After cooling to room temperature, the mixture is filtered and the filtrate extracted with CH2Cl2. The combined extracts are dried over MgSO4, filtered, and concentrated to yield a red oil, which is subjected to Kugelrohr distillation under high vacuum at 150° C. to yield 838 mg of the title compound as a clear, light yellow oil.

المصدر