Methanol → 5-(1H-indol-2-yl)oxazole

HRID 537853ノート

反応式

HRID 537853 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=[O:11].CO.C1(C)C=CC(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[O:11][CH:25]=[N:24][CH:23]=1

参加物

6

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 96389Indole-2-carboxaldehydeHCID 161915Tosylmethyl isocyanide

生成物 1

HCID 8520455-(1H-indol-2-yl)oxazole収率 79.8%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

To a 100 mL round-bottom flask was added 1H-indole-2-carbaldehyde 18 (1.52 g, 10.48 mmol), methanol (50 mL), p-toluene sulfonylmethyl isocyanide (2.25 g, 11.52 mmol), followed by potassium carbonate (1.86 g, 13.45 mmol). The reaction mixture was stirred at reflux for about 1.5 hour and followed by TLC. The solvent was then evaporated and saturated aq.NaHCO3 was added. The resultant suspension was extracted with CH2Cl2 (3×30 mL). Combined organic layers were washed with brine, dried (anhydrous Na2SO4), and concentrated to leave a yellow solid. Crude product was further purified by silica-column chromatographed (Biotage) using Acetone:Hexane as an eluent to yield 5-(1H-indol-2-yl)oxazole 19 (1.54 g, 79% yield). MS (ES) m/z 185 (M+H+).

後処理

  1. temperatureat reflux for about 1.5 hour
  2. customThe solvent was then evaporated
  3. additionNaHCO3 was added
  4. extractionThe resultant suspension was extracted with CH2Cl2 (3×30 mL)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried (anhydrous Na2SO4)
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. customCrude product was further purified by silica-column
  10. customchromatographed (Biotage)

出典と根拠

ORDレコード
ord-15869404de6f4c1f80813ccb6ff8fef5
出典データセット
uspto-grants-2014_10
特許番号
US08865709B2

反応ノート

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