Pyridine → Methyl 3-oxoicosanoate

HRID 1609359

반응식

HRID 1609359 반응식
C[C:2]1(C)[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.N1C=CC=CC=1.[C:17](Cl)(=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]C>C(Cl)Cl>[CH3:2][O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

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

To a solution of 117 g of Meldrum's acid and 131 ml of pyridine in 1.5 l of methylene chloride, 270 ml of stearic acid chloride were added dropwise at a maximum temperature of 15° C. After stirring, the reaction mixture was washed with 4N hydrochloric acid, the aqueous phase was extracted with methylene chloride, the methylene chloride phase was dried and concentrated. The residue was taken up in methanol and stirred under reflux. After cooling, the precipitated crystals were filtered off, dissolved in methylene chloride and chromatographied on silica gel with methylene chloride to give 175 g of methyl-3-oxoeicosanoate, m.p. 52°-54° C.

후처리

  1. washthe reaction mixture was washed with 4N hydrochloric acid
  2. extractionthe aqueous phase was extracted with methylene chloride
  3. dry with materialthe methylene chloride phase was dried
  4. concentrationconcentrated
  5. stirringstirred
  6. temperatureunder reflux
  7. temperatureAfter cooling
  8. filtrationthe precipitated crystals were filtered off
  9. dissolutiondissolved in methylene chloride

출처 및 근거

ORD 기록
ord-d9ad72e1428943359ee0f700936c71d8
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05399720

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