3-Chloro-2-methyl-1-propene → HCID 22506841、化合物

HRID 985573ノート

反応式

HRID 985573 の反応式
[OH:1][C:2]1[C:3]([CH3:16])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([CH:12]=[O:13])[C:6]([CH3:15])([CH3:14])[CH2:5]2.[H-].[Na+].Cl[CH2:20][C:21]([CH3:23])=[CH2:22].[Cl-].[NH4+]>CN(C=O)C>[CH3:15][C:6]1([CH3:14])[CH2:5][C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([O:1][CH2:22][C:21]([CH3:23])=[CH2:20])[C:3]=2[CH3:16])[N:7]1[CH:12]=[O:13]

参加物

6

反応物 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22506840HCID 22506840、化合物

生成物 1

HCID 22506841HCID 22506841、化合物収率 69%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2,3-dihydro-5-hydroxy-2,2,4,7-tetramethyl-1H-indole-1-carbaldehyde (2.29 g, 10.4 mmol) in DMF (15 ml) was added 60% dispersion of sodium hydride in oil (0.42 g, 12 mmol) with cooling on ice and stirred under nitrogen atmosphere at the same temperature for 5 minutes. To the resulting mixture was added 3-chloro-2-methyl-1-propene (1.3 ml, 13 mmol) and stirred at room temperature for 30 minutes and at 60° C. for 15 minutes. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted three times with ethyl acetate. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to obtain 1.95 g of the title compound.

後処理

  1. temperaturewith cooling on ice
  2. stirringstirred at room temperature for 30 minutes and at 60° C. for 15 minutes
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from diisopropyl ether-hexane

出典と根拠

ORDレコード
ord-0cb68535f2ce41889ee67787207719b6
出典データセット
uspto-grants-2005_03
特許番号
US06872718B1

反応ノート

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