Pyridine → Methyl 3-oxoicosanoate

HRID 5626

反応式

HRID 5626 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 84502Methyl 3-oxoicosanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 117 g of Meldrum's acid and 131 ml of pyridine in 1.5 1 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 chromatographed on silica gel with methylene chloride to give 175 g of methyl-3-oxoeicosanoate, m.p. 52°-54° C.

後処理

  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
  10. customchromatographed on silica gel with methylene chloride

出典と根拠

ORDレコード
ord-3baf013c7faa44a8a67c3c1de075f233
出典データセット
uspto-grants-1993_09
特許番号
US05245056

関連ノート

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