Methyl iodide → HCID 15037140, compound

HRID 488235Notes

Reaction equation

HRID 488235 reaction equation
C([Li])CCC.N1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.O1C=C[C:14]([CH:17]=[O:18])=C1.C([Li])(CC)C.Cl[Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27].IC>C1COCC1.C1CCCCC1>[CH3:7][C:8]1[O:9][C:10]([Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:11][C:14]=1[CH:17]=[O:18]

Participants

9

Reactant 6

HCID 6328Methyl iodideHCID 8083MorpholineHCID 103513-FuraldehydeHCID 13819ChlorotriethylsilaneHCID 178418339ButyllithiumHCID 178418400CID 53628100

Product 1

HCID 15037140HCID 15037140, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

n-Butyl lithium (a 1.6 M solution in THF; 19.0 ml, 30.4 mmol) was added to a solution of morpholine (2.67 ml, 30.4 mmol) in THF (20 ml) at -78 degrees C. under argon. After 20 minutes, 3-furaldehyde (1.8 ml, 28.9 mmol) was added, followed by s-butyl-lithium (a 1.3 M solution in cyclohexane; 23.4 ml, 30.4 mmol) after another 20 minutes. Stirring was continued for 2 hours and chlorotriethylsilane (5.1 ml, 30.4 mmol) was added. After 2 hours at -78 degrees C., s Buli (23.4 ml, 30.4 mmol) was added, followed by iodomethane (5.4 ml, 86.9 mmol) after another 2 hours. The mixture was stirred at room temperature for 15 hours and quenched with ice cold dilute hydrochloric acid. Extraction with ethyl ether and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 10% diethyl ether/hexane to give the titled aldehyde.

Workup

  1. wait23.4 ml, 30.4 mmol) after another 20 minutes
  2. waitwas continued for 2 hours
  3. waitAfter 2 hours at -78 degrees C
  4. additionwas added
  5. stirringThe mixture was stirred at room temperature for 15 hours
  6. customquenched with ice cold dilute hydrochloric acid
  7. extractionExtraction
  8. customwith ethyl ether and evaporation of the
  9. dry with materialdried (magnesium sulfate)
  10. customextracts gave an oil, which
  11. customwas purified by flash chromatography on silica using 10% diethyl ether/hexane

Sources & evidence

ORD record
ord-338f06d6619a4eecaccd50b2644cc93f
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

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