Hydrochloric Acid → HCID 15037036, compound

HRID 273949Notes

Reaction equation

HRID 273949 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.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].Cl>CCCCCC.O1CCCC1.C1CCCCC1>[Si:24]([C:16]1[O:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 103513-FuraldehydeHCID 28928tert-Butyldimethylsilyl chlorideHCID 178418339ButyllithiumHCID 178418400CID 53628100

Product 1

HCID 15037036HCID 15037036, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

n-Butyl lithium (a 2.5M solution) in hexane; 8.3 ml, 20.8 mmol) was added to a solution of morpholine (1.81 ml, 20 mmol) in tetrahydrofuran (100 ml) at -78° C. under argon. After 20 minutes 3-furaldehyde (1.8 ml, 20.8 mmol) was added. After another 15 minutes, sec-butyl lithium (a 1.3M solution in cyclohexane; 16.8 ml, 21.9 mmol) was added dropwise and stirring continued at -78° C. for 1 hour before a solution of t-butyldimethylsilyl chloride (9.4 g, 62.4 mmol) in tetrahydrofuran (10 ml) was added. Stirring was continued overnight (16 hours) while the cooling bath was allowed to attain room temperature. The solution was poured into ice cold 10% (v/v) hydrochloric acid (40 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 to dryness to give a brown oil, which was distilled under high vacuum to give the title aldehyde, boiling point 80°-5°/0.5 torr., m.p. 37°-8°.

Workup

  1. addition16.8 ml, 21.9 mmol) was added dropwise
  2. additionwas added
  3. stirringStirring
  4. waitwas continued overnight
  5. custom(16 hours)
  6. customto attain room temperature
  7. stirringafter stirring at 0° for 10 minutes
  8. customthe layers were separated
  9. extractionThe aqueous phase was extracted with diethyl ether
  10. dry with materialdried (magnesium sulfate)
  11. customevaporated to dryness
  12. customto give a brown oil, which
  13. distillationwas distilled under high vacuum

Sources & evidence

ORD record
ord-73be25ac479747289008dd267a9af58b
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Reaction notes

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