反応式
[CH3:1][C@@H:2]([CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[N:9]2)[CH2:3][OH:4].CC1(C)N([O])C(C)(C)CCC1.[K+].[Br-].Cl[O-].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][C@@H:2]([CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[N:9]2)[CH:3]=[O:4]参加物
実験手順
A solution of crude (S)-2-methyl-3-quinoxalin-6-yl-propan-1-ol (3.68 g, 18.19 mmol) in toluene (37 ml) is treated with TEMPO (28.4 mg, 0.152 mmol) and KBr (216.5 mg, 1.82 mmol) in 0.9 ml water. 37 ml of a 0.5 M sodiumhypochlorite solution of pH 8-9 (prepared by mixing 34 ml 0.75 M sodiumhypochlorite solution with 16 ml water and 0.85 g NaHCO3) is added dropwise over 20 minutes at 5° to 8°. After 5 minutes stifling at 0°, the two phase mixture is filtered over Hyflo, the phases separated, the organic phase washed with a solution of 116 mg KI in 15 ml 1 N HCl, then 15 ml of a 5% Na2S2O3 solution and finally 15 ml brine. Drying over Na2SO4 and evaporation afford crude aldehyde. MPLC purification (silicagel, EtOAc/hexane 2:1) yield pure (S)-2-Methyl-3-quinoxalin-6-yl-propionaldehyde as a slightly yellow clear oil. TLC (silicagel, EtOAc/hexanes 2:1): rf 0.37.
後処理
- additionis added dropwise over 20 minutes at 5° to 8°
- filtrationthe two phase mixture is filtered over Hyflo
- customthe phases separated
- washthe organic phase washed with a solution of 116 mg KI in 15 ml 1 N HCl
- dry with materialDrying over Na2SO4 and evaporation
- customafford crude aldehyde
- customMPLC purification (silicagel, EtOAc/hexane 2:1)
出典と根拠
- ORDレコード
- ord-e866dcd34a5f45ed84f6a4be0e9be93f
- 出典データセット
- uspto-grants-2003_10
- 特許番号
- US06635647B2
関連ノート
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