Diethyl Ether → (1-Hydroxymethylcyclopropyl)acetic acid methyl ester

HRID 326941

反応式

HRID 326941 の反応式
C([O:9][CH2:10][C:11]1([CH2:14][C:15]#N)[CH2:13][CH2:12]1)(=O)C1C=CC=CC=1.[OH-:17].[K+].[N+](=C)=[N-].CC[O:24][CH2:25]C>C(O)C.CCCCCC>[OH:9][CH2:10][C:11]1([CH2:14][C:15]([O:24][CH3:25])=[O:17])[CH2:12][CH2:13]1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 29941744[1-(Cyanomethyl)cyclopropyl]methyl benzoate

生成物 1

HCID 29941748(1-Hydroxymethylcyclopropyl)acetic acid methyl ester収率 50%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8058Hexane溶媒

反応条件

温度
10 °C

実験手順

The nitrile of Step 3 (0.388 mol) was dissolved in ethanol (400 mL), 8N KOH (800 mL) was added and the reaction mixture was heated to reflux overnight. Most of the ethanol was evaporated and ice was added to the mixture. Concentrated HCl was added (600 mL) dropwise at 0° C. (without warming over 10° C. inside the solution) until obtention of pH≃1. The acid was then extracted with EtOAc two times and the organic phases were washed 2 times with brine and dried over Na2SO4. The solvent was evaporated and the solid was dissolved in THF (500 mL). A solution of diazomethane in Et2O (about 1.7 L, 0.85 mol) was added at 0° C. until the yellow color remained and no more acid can be seen by TLC. The solvent was evaporated and the residual oil was purified by flash chromatography using 1:1 to 2:1 EtOAc:hexane to yield 28.2 g, (50% yield) of the title compound.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customMost of the ethanol was evaporated
  4. additionice was added to the mixture
  5. additionConcentrated HCl was added (600 mL) dropwise at 0° C. (
  6. extractionThe acid was then extracted with EtOAc two times
  7. washthe organic phases were washed 2 times with brine
  8. dry with materialdried over Na2SO4
  9. customThe solvent was evaporated
  10. dissolutionthe solid was dissolved in THF (500 mL)
  11. customThe solvent was evaporated
  12. customthe residual oil was purified by flash chromatography

出典と根拠

ORDレコード
ord-b665b95d7daa4ee0a6eb7d0f5b9b26c2
出典データセット
uspto-grants-1993_12
特許番号
US05270324

関連ノート

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