Tridecanoic acid → Methyl 4-tridecanoylpyrrole-2-carboxylate

HRID 465397

반응식

HRID 465397 반응식
[C:1](O)(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[NH:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:29]([O:31][CH3:32])=[O:30]>C(Cl)Cl.CN(C)C=O>[C:1]([C:27]1[CH:26]=[C:25]([C:29]([O:31][CH3:32])=[O:30])[NH:24][CH:28]=1)(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

참가 물질

7

반응물 4

HCID 12530Tridecanoic acidHCID 24386Thionyl ChlorideHCID 136930Methyl pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 15023257Methyl 4-tridecanoylpyrrole-2-carboxylate수율 83.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매4회

실험 절차

In 480 ml of methylene chloride, were dissolved 102.9 g (0.48 mol) of tridecanoic acid, to which 52.6 ml (0.72 mol) of thionyl chloride and 0.2 ml of N,N-dimethylformamide were added to obtain a solution. The solution was allowed to stand over night and was evaporated under a reduced pressure. The remaining oil was added to 400 ml of methylene chloride containing 106.6 g (0.8 mol) of anhydrous aluminum chloride, to which 200 ml of methylene chloride solution containing 50.05 g (0.4 mol) of methyl pyrrole-2-carboxylate was added dropwise in 40 minutes at a temperature of 3° to 9° C. After the addition, the temperature of the mixture was elevated slowly up to room temperature and the mixture was stirred for 2 hours. Then, the mixture was poured into 800 ml of ice-water, and 1000 ml of methylene chloride was added thereto to dissolve all the crystals precipitated, followed by liquid separation. The organic layer was washed with water three times, dried over anhydrous magnesium sulfate and condensed under a reduced pressure. The residue was recrystallized from 400 ml of ethyl acetate and 400 ml of hexane to obtain 107.2 g of methyl 4-tridecanoylpyrrole-2-carboxylate as white crystals. The yield was 83% and the melting point was 92° to 93° C.

후처리

  1. customto obtain a solution
  2. waitto stand over night
  3. customwas evaporated under a reduced pressure
  4. additionwas added dropwise in 40 minutes at a temperature of 3° to 9° C
  5. additionAfter the addition
  6. customwas elevated slowly up to room temperature
  7. additionwas added
  8. dissolutionto dissolve all the crystals
  9. customprecipitated
  10. customfollowed by liquid separation
  11. washThe organic layer was washed with water three times
  12. dry with materialdried over anhydrous magnesium sulfate and condensed under a reduced pressure
  13. customThe residue was recrystallized from 400 ml of ethyl acetate and 400 ml of hexane

출처 및 근거

ORD 기록
ord-e27f490ad8e34456a02da780c70f4026
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153217

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