Hydrochloric Acid → HCID 15037036, compound

HRID 2107824Notes

Reaction equation

HRID 2107824 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° under argon. After 20 min. 3-furaldehyde (1.8 ml, 20.8 mmol) was added. After another 15 min., sec-butyl lithium (a 1.3M solution in cyclohexane; 16.8 ml, 21.9 mmol) was added dropwise and stirring continued at -78° for 1 hour before a solution of t-butyl dimethylsilyl 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 min., 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 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. waitAfter another 15 min.
  2. addition16.8 ml, 21.9 mmol) was added dropwise
  3. additionwas added
  4. stirringStirring
  5. waitwas continued overnight
  6. custom(16 hours)
  7. customto attain room temperature
  8. stirringafter stirring at 0° for 10 min.
  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 a brown oil, which
  14. distillationwas distilled under high vacuum

Sources & evidence

ORD record
ord-963683bafb9842e29c8ac57efab88355
Source dataset
uspto-grants-1990_06
Patent number
US04935530

Reaction notes

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