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

HRID 1090923

반응식

HRID 1090923 반응식
[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]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 150371484-Phenyl-3-furaldehyde2회HCID 178418339Butyllithium2회

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매2회

실험 절차

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 argon. After 20 minutes the solution was cooled to -78 degrees 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 1.6M 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 10% (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.

후처리

  1. temperatureAfter 20 minutes the solution was cooled to -78 degrees
  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 10% (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

출처 및 근거

ORD 기록
ord-daa206959471416aa1bca7fa73c966f7
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082954

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