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

HRID 488237

반응식

HRID 488237 반응식
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

참가 물질

9

반응물 5

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

생성물 1

HCID 150371493-Phenyl-2-triethylsilyl-4furaldehyde

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 8078Cyclohexane용매

실험 절차

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. (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.

후처리

  1. temperatureAfter 15 minutes the solution was cooled to -78 degrees
  2. addition(517 mg, 3.01 mmol) was added
  3. temperatureThis mixture was warmed to 0 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

출처 및 근거

ORD 기록
ord-85a43c7db76f4054ac34b3386eef8203
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298633

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