1,4-Dimethoxybutan-2-one → HCID 21094561, 화합물

HRID 1350539노트

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HRID 1350539 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:13](=[CH:14][N:15]([CH3:18])[N:16]=3)[CH:12]=[CH:11][CH:10]=2)=[C:5]([CH3:19])[CH:4]=1.[Li]CCCC.[CH3:25][O:26][CH2:27][C:28](=[O:33])[CH2:29][CH2:30][O:31][CH3:32]>C1COCC1.CCOC(C)=O>[CH3:25][O:26][CH2:27][C:28]([C:14]1[N:15]([CH3:18])[N:16]=[C:17]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH3:19])([OH:33])[CH2:29][CH2:30][O:31][CH3:32]

참가 물질

6

반응물 3

HCID 2669141,4-Dimethoxybutan-2-oneHCID 210946097-(4-Methoxy-2-methyl-phenyl)-2-methyl-2H-indazoleHCID 178418339Butyllithium

생성물 1

HCID 21094561HCID 21094561, 화합물수율 65%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

Indazole 4c (0.29 g, 0.79 mMol) was dissolved in 5 mL dry THF under a nitrogen atmosphere and cooled to −78° C. n-BuLi (0.4 mL of 2.5 M hexane solution, 1 mMol) was added dropwise via syringe, and stirred at −78° C. for 10 minutes. 1,4-dimethoxy-2-butanone (0.16 g, 1.18 mMol) was added dropwise at −78° C. and then the reaction mixture was allowed to warm to rt. The reaction mixture was diluted with EtOAc (50 mL) and washed successively with saturated ammonium chloride solution, brine and dried over magnesium sulfate. Evaporation of the solvent afforded crude material which was flash chromatographed on silica and eluted with hexane:EtOAc (3:1) which afforded 27c as an oil (0.196 g; 65%).

후처리

  1. additionwas added dropwise via syringe
  2. temperatureto warm to rt
  3. washwashed successively with saturated ammonium chloride solution, brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customafforded crude material which
  7. customchromatographed on silica
  8. washeluted with hexane:EtOAc (3:1) which

출처 및 근거

ORD 기록
ord-ff809157bae8413b971bc99d7eb0a199
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214699B2

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