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

HRID 403604ノート

反応式

HRID 403604 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-5f52743799ff4853b0b88731e520f277
出典データセット
uspto-grants-2014_06
特許番号
US08748446B2

反応ノート

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