Acetone → 5-Tert-butyloxazole-4-carboxaldehyde

HRID 1092745노트

반응식

HRID 1092745 반응식
[C:1]([C:5]1[O:9][CH:8]=[N:7][C:6]=1[CH:10]=C(O)C(O)=O)([CH3:4])([CH3:3])[CH3:2].CC(C)=[O:18]>O=[Mn]=O>[C:1]([C:5]1[O:9][CH:8]=[N:7][C:6]=1[CH:10]=[O:18])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 2

HCID 180AcetoneHCID 665900433-(5-tert-Butyloxazol-4-yl)-2-hydroxyacrylic acid

생성물 1

HCID 210314885-Tert-butyloxazole-4-carboxaldehyde

시약·촉매·용매 1

HCID 14801Manganese dioxide촉매

실험 절차

To a solution of oxazole alcohol 3 (9.9 g, 64 mmol) in acetone (200 mL, Aldrich, Cat. No. 179124) was added MnO2 (27.7 g, 319 mmol, 5 equiv., Wako Pure Chemical, Osaka, Japan, Cat. No. 138-09675), and the mixture was stirred at room temperature overnight. After celite filtration to remove MnO2, the solvent was removed by evaporation, and the residual pale brown oil was dissolved in CHCl3 and applied to silica-gel column chromatography (prepared with CHCl3), then eluted with CHCl3:MeOH (100:1 to 50:1), to give an pale yellow oil of aldehyde 4 (5.54 g, 57% (38% in two steps)). Rf 0.65 (CHCl3:MeOH=10:0.5), 1H NMR (300 MHz CDCl3) δ 10.10 (s, 1H), 7.77 (s, 1H), 1.47 (s, 9H); HRMS (EI): m/z 153.0794 (M+) (Calcd for C8H11NO2: 153.0790).

후처리

  1. filtrationAfter celite filtration
  2. customto remove MnO2
  3. customthe solvent was removed by evaporation
  4. dissolutionthe residual pale brown oil was dissolved in CHCl3
  5. customapplied to silica-gel column chromatography (prepared with CHCl3)
  6. washeluted with CHCl3:MeOH (100:1 to 50:1)

출처 및 근거

ORD 기록
ord-d420428afd6c4db9bfd7d3737c272aa2
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129527B2

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