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

HRID 22427

반응식

HRID 22427 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8058Hexane용매

반응 조건

온도
10 °C

실험 절차

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 approx. 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 could 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. 1H NMR (CDCl3) δ0.55 (4H, m), 2.45 (2H, s), 2.55 (1H, t), 3.5 (2H, d), 3.70 (3H, s).

후처리

  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

출처 및 근거

ORD 기록
ord-6580c9e7e82d451093839be42a1b70af
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428033

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