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

HRID 2166385

반응식

HRID 2166385 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b0e953cf334b4c729f52b761f0c0481f
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04945099

연결된 노트

불러오는 중…