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

HRID 413519ノート

反応式

HRID 413519 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-40a0d57aed3147baa8434d32b8677ce7
出典データセット
uspto-grants-2003_05
特許番号
US06566526B2

反応ノート

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