1,4-Dimethoxybutan-2-one → HCID 21094561、化合物

HRID 1350539ノート

反応式

HRID 1350539 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 21094561HCID 21094561、化合物収率 65%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ff809157bae8413b971bc99d7eb0a199
出典データセット
uspto-grants-2007_05
特許番号
US07214699B2

反応ノート

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