Methyl iodide → 2-Methyl-4-phenyl-3-furaldehyde

HRID 1109903

Reaction equation

HRID 1109903 reaction equation
[CH2:1]([Li])CCC.CNCCN(C)C.[C:13]1([C:19]2[C:23]([CH:24]=[O:25])=[CH:22][O:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.IC>CCCCCC.O1CCCC1>[CH3:1][C:22]1[O:21][CH:20]=[C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:23]=1[CH:24]=[O:25]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 150371484-Phenyl-3-furaldehyde2×HCID 178418339Butyllithium2×

Product 1

HCID 150371592-Methyl-4-phenyl-3-furaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

n-Butyllithium (a 1.6 m solution in hexane, 2.43 ml, 3.89 mmol) was added to a solution of trimethylethylenediamine (397 mg, 3.89 mmol) in tetrahydrofuran (25 ml) at 0 degrees under 24 argon. After 20 minutes the solution was cooled to -78 degres and 3-phenyl-4-furaldehyde (Compound 18, 608 mg, 3.35 mmol) was added. This mixture was allowed to gradually warm to -20 degrees and stirred for 11/2 hours, then recooled to -78 degrees before n-butyllithium (a 1.6 M solution in hexane, 2.43 ml, 3.89 mmol) was added dropwise. The stirring mixture was again gradually warmed to -20 degrees and stirred for 2 hours before iodomethane (2.56 g 17.67 mmol) was added. After stirring for 18 hours at -20 degrees the reaction was quenched with ice-cold lot (v/v) hydrochloric acid and the organics were extracted into ethyl ether. The combined fractions were washed with saturated sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 20% ethyl ether/hexanes to give the title aldehyde.

Workup

  1. additionwas added
  2. temperatureto gradually warm to -20 degrees
  3. additionwas added dropwise
  4. temperatureThe stirring mixture was again gradually warmed to -20 degrees
  5. additionwas added
  6. stirringAfter stirring for 18 hours at -20 degrees the reaction
  7. customwas quenched with ice-cold lot (v/v) hydrochloric acid
  8. extractionthe organics were extracted into ethyl ether
  9. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
  10. customEvaporation of the
  11. dry with materialdried (magnesium sulfate)
  12. customextracts gave an oil which
  13. customwas purified by flash chromatography on silica using 20% ethyl ether/hexanes

Sources & evidence

ORD record
ord-650a969c8d384013a2d1a4d32f250583
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Linked notes

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