Potassium Iodide → 5-(2,4-Diacetyl-5-hydroxyphenoxy)pentanenitrile

HRID 2166385

反応式

HRID 2166385 の反応式
[C:1]([C:4]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[C:7]([OH:8])=[CH:6][C:5]=1[OH:14])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27].[I-].[K+]>>[C:1]([C:4]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[C:7]([OH:8])=[CH:6][C:5]=1[O:14][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])(=[O:3])[CH3:2]

参加物

5

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 750974,6-DiacetylresorcinolHCID 794355-Bromopentanenitrile

生成物 1

HCID 148200535-(2,4-Diacetyl-5-hydroxyphenoxy)pentanenitrile収率 24.2%

実験手順

A mixture of 582 mg of 4,6-diacetylresorcinol, 460 mg of potassium carbonate, 530 mg of 5-bromopentanenitrile and 0.2 g of potassium iodide was heated at reflux overnight. The mixture was concentrated in vacuo and partitioned between ethyl acetate and dilute hydrochloric acid. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with 40% ethyl acetate in hexane to provide 200 mg of the desired title product, m.p.=105°-106° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between ethyl acetate and dilute hydrochloric acid
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with 40% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-b0e953cf334b4c729f52b761f0c0481f
出典データセット
uspto-grants-1990_07
特許番号
US04945099

関連ノート

読み込み中…