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

HRID 1736515Notes

Reaction equation

HRID 1736515 reaction equation
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]

Participants

10

Reactant 6

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

Product 1

HCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

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-triethylsily-3-furaldehyde as a pale yellow oil, boiling point 85°-90°/0.4 torr.

Workup

  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

Sources & evidence

ORD record
ord-3f4451e259de446eb7a8fefb7062f06b
Source dataset
uspto-grants-1996_07
Patent number
US05541221

Reaction notes

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