Chlorotriethylsilane → 3-Phenyl-2-triethylsilyl-4furaldehyde

HRID 2081343Notes

Reaction equation

HRID 2081343 reaction equation
C([Li])CCC.CN1CCNCC1.[C:13]1([C:19]2[C:20]([CH:24]=[O:25])=[CH:21][O:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([Li])(CC)C.Cl[Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34]>CCCCCC.O1CCCC1.C1CCCCC1>[C:13]1([C:19]2[C:20]([CH:24]=[O:25])=[CH:21][O:22][C:23]=2[Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

9

Reactant 5

HCID 13819ChlorotriethylsilaneHCID 531671-MethylpiperazineHCID 150371484-Phenyl-3-furaldehyde2×HCID 178418339ButyllithiumHCID 178418400CID 53628100

Product 1

HCID 150371493-Phenyl-2-triethylsilyl-4furaldehyde

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

n-Butyllithium (a 1.42 M solution in hexane, 2.33 ml, 3.31 mmol) was added to a solution of 1-methylpiperazine (331 mg. 3.31 mmol) in tetrahydrofuran (15 ml) at 0 degrees under argon. After 15 minutes the solution was cooled to-78 degrees and 4-phenyl-3-furaldehyde (Compound 54 517 mg, 3.01 mmol) was added. This mixture was warmed to 0 degrees and stirred for 15 minutes, then recooled to-78 degrees before sec-butyllithium (a 1.3 M solution in cyclohexane, 2.77 ml, 3.61 mmol) was added dropwise. This solution was stirred 12 hours at-78 degrees C. before chlorotriethylsilane (1.81 g, 12.02 mmol) was added. The mixture was allowed to warm gradually to room temperature and stirred an additional 11/2 hours. The reaction was quenched with ice-cold 5% (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 10% ethyl acetate/hexanes to give the title aldehyde.

Workup

  1. additionwas added
  2. temperatureThis mixture was warmed to 0 degrees
  3. custom78 degrees
  4. additionwas added dropwise
  5. stirringThis solution was stirred 12 hours at-78 degrees C
  6. stirringstirred an additional 11/2 hours
  7. customThe reaction was quenched with ice-cold 5% (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 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-760c8a5f6687431190949b87430d0c26
Source dataset
uspto-grants-1993_02
Patent number
US05183906

Reaction notes

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