Sulfuric Acid → 6-Chloropyridine-3-carbaldehyde
반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][N:3]=1.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.[OH:26]S(O)(=O)=O>CO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:6]=[O:26])=[CH:8][CH:9]=1참가 물질
6
반응 조건
- 온도
- 0 °C
실험 절차
Combine 6-chloro-nicotino-nitrile (1.00 g, 7.21 mmol) and toluene (24 mL). Cool the resulting solution at 0° C. and add DIBAL-H (1.0 M in toluene, 7.58 mL, 7.58 mmol) dropwise. Stir the resulting red solution at 0° C. for 1 h. Then, add methanol (2 mL) followed by H2SO4 (aq. 2.0 M, 6 mL). Stir for 1 h at rt. Add CHCl3:isopropanol (3/1, 15 mL) and wash with Rochelle's salt solution (20 mL), followed by NaHCO3 (20 mL) and brine. Dry the combined organic layers over magnesium sulfate, filter and concentrate. Purify by flash chromatography (EtOAc/hexanes 10%) to give the title compound (530 mg, 62%).
후처리
- stirringStir for 1 h at rt
- washAdd CHCl3:isopropanol (3/1, 15 mL) and wash with Rochelle's salt solution (20 mL)
- dry with materialDry the combined organic layers over magnesium sulfate
- filtrationfilter
- concentrationconcentrate
- customPurify by flash chromatography (EtOAc/hexanes 10%)
출처 및 근거
- ORD 기록
- ord-11f65d50ccb94616be56241ee9ec4429
- 출처 데이터셋
- uspto-grants-2008_06
- 특허 번호
- US07381719B2
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