Pyridine → Methyl 3-oxoicosanoate

HRID 257106

반응식

HRID 257106 반응식
[C:1](Cl)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C.C[C:22]1(C)[O:29][C:27](=[O:28])[CH2:26][C:24](=[O:25])O1.N1C=CC=CC=1>C(Cl)Cl>[O:25]=[C:24]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:26][C:27]([O:29][CH3:22])=[O:28]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 8212Stearoyl chlorideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

생성물 1

HCID 84502Methyl 3-oxoicosanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

270 ml of stearoyl chloride were added dropwise at a maximum of 150° C. to a solution of 117 g of Meldrum's acid and 131 ml of pyridine in 1.5 I of methylene chloride. After stirring the reaction mixture was washed with 4N hydrochloric acid, the aqueous phase was back-extracted with methylene chloride and the methylene chloride phase was dried and concentrated. The residue was taken up in methanol and stirred under reflux. After cooling the separated crystals were filtered off, dissolved in methylene chloride and chromatographed on silica gel with methylene chloride. There were obtained 175 g of methyl 3-oxoeicosanoate, m.p. 52°-54° C.

후처리

  1. washwas washed with 4N hydrochloric acid
  2. extractionthe aqueous phase was back-extracted with methylene chloride
  3. dry with materialthe methylene chloride phase was dried
  4. concentrationconcentrated
  5. stirringstirred
  6. temperatureunder reflux
  7. temperatureAfter cooling the separated crystals
  8. filtrationwere filtered off
  9. dissolutiondissolved in methylene chloride
  10. customchromatographed on silica gel with methylene chloride

출처 및 근거

ORD 기록
ord-03979860f138403b88e7e955a35ff59d
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260310

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