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

HRID 2247837Notes

Reaction equation

HRID 2247837 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. custom-78°
  4. customfor about 2 hours
  5. additionwas added
  6. stirringStirring
  7. waitwas continued overnight
  8. custom(14 hours)
  9. customto attain room temperature
  10. stirringafter stirring at 0° for 10 minutes
  11. customthe layers were separated
  12. extractionThe aqueous phase was extracted with diethyl ether
  13. dry with materialdried (magnesium sulfate)
  14. customevaporated down
  15. customto give an oil, which
  16. distillationwas distilled under high vacuum

Sources & evidence

ORD record
ord-a32c6a9af30b4dada6786a79dc6d5390
Source dataset
uspto-grants-1991_08
Patent number
US05037811

Reaction notes

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