3-Methyl-2-butanone → 4,5,6-triiodo-2,3,3-trimethyl-3H-indole

HRID 508293ノート

反応式

HRID 508293 の反応式
[I:1][C:2]1[CH:3]=[C:4]([NH:10]N)[CH:5]=[C:6]([I:9])[C:7]=1[I:8].[CH3:12][CH:13]([CH3:17])[C:14](=O)[CH3:15]>C(O)(=O)C>[I:1][C:2]1[C:7]([I:8])=[C:6]([I:9])[CH:5]=[C:4]2[C:3]=1[C:13]([CH3:17])([CH3:12])[C:14]([CH3:15])=[N:10]2

参加物

4

反応物 2

HCID 112513-Methyl-2-butanoneHCID 866953333,4,5-Triiodophenylhydrazine

生成物 1

HCID 717360084,5,6-triiodo-2,3,3-trimethyl-3H-indole収率 27.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

2 g of 3,4,5-triiodophenylhydrazine, and 0.86 g (10 mmol) of 3-methyl-2-butanone were refluxed in 15 mL of acetic acid for 16 hours. The acetic acid was evaporated, the residue was dissolved in chloroform, washed with aqueous solutions of NaHCO3, followed by Na2S2O3 and water. The organic layer was dried and chloroform was removed under reduced pressure by a rotary evaporator. The residue was column purified (Silica gel 60, 0-2% methanol-chloroform) to give 0.6 g of 4,5,6-triiodo-2,3,3-trimethyl-3H-indole. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 8.04 (1H, s, arom.), 2.19 (3H, s, 2-CH3), 1.30 (6H, s, C(CH3)2).

後処理

  1. customThe acetic acid was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with aqueous solutions of NaHCO3
  4. customThe organic layer was dried
  5. customchloroform was removed under reduced pressure by a rotary evaporator
  6. custompurified (Silica gel 60, 0-2% methanol-chloroform)

出典と根拠

ORDレコード
ord-c8f6c027dbf84cdbb665f7d3bde2b94e
出典データセット
uspto-grants-2015_08
特許番号
US09095612B2

反応ノート

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