Hydrochloric Acid → 3-Furancarboxaldehyde, 5-(triethylsilyl)-

HRID 273948

반응식

HRID 273948 반응식
C([Li])CCC.N1CCOCC1.[O:12]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13]1.C([Li])(CC)C.[CH2:24]([Si:26](Cl)([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25].Cl>CCCCCC.O1CCCC1.C1CCCCC1>[CH2:24]([Si:26]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:16]1[O:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=1)[CH3:25]

참가 물질

10

반응물 6

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 103513-FuraldehydeHCID 13819ChlorotriethylsilaneHCID 178418339ButyllithiumHCID 178418400CID 53628100

생성물 1

HCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 8078Cyclohexane용매

실험 절차

n-Butyl lithium (a 2.5M solution in hexane; 30.6 ml, 76.5 mmol) was added to a solution of morpholine (6.66 ml, 76.5 mmol) in tetrahydrofuran (500 ml) at -78° under argon. After 15 minutes, 3-furaldehyde (6.3 ml, 72.8 mmol) was added. After another 20 minutes, sec-butyl lithium (a 1.3M solution in cyclohexane; 59.0 ml, 76.5 mmol) was added dropwise and stirring continued at -78° for about 2 hours before triethylsilylchloride (13.4 ml, 80.1 mmol) was added. Stirring was continued overnight (14 hours) while the cooling bath was allowed to attain room temperature. The solution was poured into ice cold 10% (v/v) hydrochloric acid (100 ml) and after stirring at 0° for 10 minutes, the layers were separated. The aqueous phase was extracted with diethyl ether. All the organic phases were combined, dried (magnesium sulfate) and evaporated down to give an oil, which was distilled under high vacuum to give the 5-triethylsilyl-3-furaldehyde as a pale yellow oil, boiling point 85°-90°/0.4 torr.

후처리

  1. waitAfter another 20 minutes
  2. addition59.0 ml, 76.5 mmol) was added dropwise
  3. additionwas added
  4. stirringStirring
  5. waitwas continued overnight
  6. custom(14 hours)
  7. customto attain room temperature
  8. stirringafter stirring at 0° for 10 minutes
  9. customthe layers were separated
  10. extractionThe aqueous phase was extracted with diethyl ether
  11. dry with materialdried (magnesium sulfate)
  12. customevaporated down
  13. customto give an oil, which
  14. distillationwas distilled under high vacuum

출처 및 근거

ORD 기록
ord-6404b255f0564903b90120738c6eb40b
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387606

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