تفاعل #1833279

ord-5702134106ae4ee1823488ad433434f3

معادلة التفاعل

COC(=O)c1ccc(C)nc1
methyl 6-methylnicotinate
[H-].[Na+]
NaH
Cc1ccccc1
toluene
CCOC(C)=O.COC(=O)c1ccc(C)nc1
methyl 6-methylnicotinate ethyl acetate
CCOC(C)=O.COC(=O)c1ccc(C)nc1
methyl 6-methylnicotinate ethyl acetate
CC(=O)c1ccc(C)nc1
2-methyl-5-acetylpyridine
المردود 65.0%

المذيبات

ظروف التفاعل

درجة الحرارة
80°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONwas added
  2. 2
    workup.ADDITIONAfter addition
  3. 3
    workup.WAITthe reaction was conducted at 80° C. for 8 h
  4. 4
    درجة الحرارةcooled to room temperature
  5. 5
    استخلاصthe water layer was extracted with ethyl acetate three times, 200 ml per time
  6. 6
    أخرىto evaporate ethyl acetate
  7. 7
    workup.ADDITION10% H2SO4 aqueous solution 400 ml was added
  8. 8
    درجة الحرارةheated to 110° C.
  9. 9
    درجة الحرارةrefluxed for 2 h
  10. 10
    درجة الحرارةcooled to room temperature
  11. 11
    ترشيحto 9, suction filtration
  12. 12
    غسيلthe filter cake was washed with ethyl acetate
  13. 13
    استخلاصThe filtrate was extracted with ethyl acetate four times
  14. 14
    أخرىrotary evaporated
  15. 15
    أخرىto dry

الإجراء التجريبي

50 g of methyl 6-methylnicotinate was dissolved in 200 ml of ethyl acetate; 60% NaH 26.5 g, toluene 400 ml and DMF 34 ml were added to a three-necked bottle, 10% methyl 6-methylnicotinate ethyl acetate solution 20 ml was added, heated to 80° C., stirred for 0.5 h. To the reaction bottle, the residual methyl 6-methylnicotinate ethyl acetate solution was added dropwise slowly within about 1.5 h. After addition, the reaction was conducted at 80° C. for 8 h. The reaction stopped, cooled to room temperature. 300 ml of water was added to the reaction bottle, skimmed, the water layer was extracted with ethyl acetate three times, 200 ml per time. All ethyl acetate layers were combined, distillated at a reduced pressure to evaporate ethyl acetate, then 10% H2SO4 aqueous solution 400 ml was added, heated to 110° C., refluxed for 2 h. The reaction was then stopped, cooled to room temperature. Solid K2CO3 was used to adjust PH to 9, suction filtration was performed, the filter cake was washed with ethyl acetate. The filtrate was extracted with ethyl acetate four times, combined and rotary evaporated to dry, to obtain 35 g of 2-methyl-5-acetylpyridine, yield was about 65%.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09149467B2uspto-grants-2015_10