Methyl iodide → HCID 15037140, compound

HRID 273952Notes

Reaction equation

HRID 273952 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 1.6M 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 1.3M 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 diethylether 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 diethylether 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-e43e325d5d25415abd66e648b2a22c21
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Reaction notes

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