Water → 2-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionitrile

HRID 413519

반응식

HRID 413519 반응식
Br[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][Cl:15])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C[Si]([C:21]#[N:22])(C)C.[Sn](Cl)(Cl)(Cl)Cl.O>C(Cl)Cl>[Cl:15][CH2:14][CH2:13][CH2:12][C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:2]([CH3:4])([CH3:3])[C:21]#[N:22])=[CH:10][CH:9]=1)=[O:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanideHCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

생성물 1

HCID 155128302-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dissolve 1-[4-(1-bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one (2.00 g, 6.59 mmol) in anhydrous methylene chloride (20 mL) and place under an argon atmosphere. Add trimethylsilyl cyanide (1.10 mL, 8.25 mmol) followed by tin (IV) chloride (0.20 mL, 1.7 mmol) via syringe. Stir at reflux for 1 hour, add water (20 mL) and stir for an additional ½ hour. Separate the layers and extract the aqueous layer with methylene chloride. Combine the organic layers, wash with brine, dry (MgSO4), filter and evaporate the solvent in vacuo. Purify by silica gel chromatography (15% ethyl acetate/hexane) to give the title compound as a white solid; mp 79-80° C.

후처리

  1. temperatureat reflux for 1 hour
  2. stirringstir for an additional ½ hour
  3. customSeparate the layers
  4. extractionextract the aqueous layer with methylene chloride
  5. washwash with brine
  6. dry with materialdry (MgSO4)
  7. filtrationfilter
  8. customevaporate the solvent in vacuo
  9. customPurify by silica gel chromatography (15% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-40a0d57aed3147baa8434d32b8677ce7
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566526B2

연결된 노트

불러오는 중…