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

HRID 1681533

反応式

HRID 1681533 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒2 回

実験手順

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 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.

後処理

  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

出典と根拠

ORDレコード
ord-0b8e5e2bb2fd4465b929f4b13517a01a
出典データセット
uspto-grants-1992_12
特許番号
US05171863

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