Ammonium Chloride → HCID 178486613、化合物

HRID 392587ノート

反応式

HRID 392587 の反応式
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]([Li])(C)([CH3:9])[CH3:8].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH:20]=[C:19]([CH:26]=[O:27])[CH:18]=[CH:17]2.[Cl-].[NH4+]>C1COCC1.CCCCC>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH:20]=[C:19]([C:26]([C:2]1[N:3]=[CH:4][NH:5][CH:6]=1)([OH:27])[CH:7]([CH3:9])[CH3:8])[CH:18]=[CH:17]2

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 315054MLS003115188HCID 178418306HCID 178418306、化合物HCID 178418934HCID 178418934、化合物

生成物 1

HCID 178486613HCID 178486613、化合物

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

4-Bromo-1H-imidazol (1.95 g) was dissolved in THF (30 ml) and the mixture was cooled to −78° C. A solution (1.7 M; 20 ml) of t-butyllithium in pentane was added. The mixture was stirred at 0° C. for 1.5 h and again cooled to −78° C. A solution (20 ml) of 6,7-dimethoxy-2-formyl naphthalene (3.32 g) in THF was added and the mixture was warmed from −78° C. to room temperature. The mixture was stirred at room temperature for 16 h and aqueous solution of ammonium chloride was added. The mixture was extracted with ethyl acetate and the organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (eluate, dichloromethane:methanol=10:1) and crystallized from dichloromethane-methanol to give the title compound (1.31 g) as a colorless solid.

後処理

  1. temperatureagain cooled to −78° C
  2. temperaturethe mixture was warmed from −78° C. to room temperature
  3. stirringThe mixture was stirred at room temperature for 16 h
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluate, dichloromethane:methanol=10:1)
  8. customcrystallized from dichloromethane-methanol

出典と根拠

ORDレコード
ord-888f94468acc44caba01f1874b675f03
出典データセット
uspto-grants-2004_10
特許番号
US06800778B1

反応ノート

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