Allyl bromide → 2-Methyl-2-phenylpent-4-enenitrile

HRID 400644

反応式

HRID 400644 の反応式
[C:1]1([CH:7]([CH3:10])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>CS(C)=O.C1COCC1.[Cl-].[NH4+]>[CH3:10][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:23][CH:22]=[CH2:21])[C:8]#[N:9]

参加物

7

反応物 3

HCID 7841Allyl bromideHCID 157612-PhenylpropionitrileHCID 2724254Sodium bis(trimethylsilyl)amide

生成物 1

HCID 105113792-Methyl-2-phenylpent-4-enenitrile収率 99.6%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of 2-phenylpropionitrile (4.04 g, 30.79 mmol) in 40 mL of DMSO was added 34 mL (34 mmol) of a 1 M solution of sodium bis(trimethylsilyl)amide (NaHMDS) in THF over a 5 minute period. After 10 minutes, allyl bromide (6 mL, 69.33 mmol) was added dropwise (exothermic). The mixture was cooled with an ice-water bath. The mixture stirred for 20 minutes, becoming a solid mass. An additional 20 mL of DMSO was added. After 10 minutes, the mixture was diluted with 200 mL of ammonium chloride and extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with six 75 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 5.25 g (99.5% yield) of 2-methyl-2-phenylpent-4-enenitrile as yellow oil which was used without further purification.

後処理

  1. temperatureThe mixture was cooled with an ice-water bath
  2. waitAfter 10 minutes
  3. extractionextracted with three 100 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with six 75 mL portions of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-92b51de5a53942ec8f909e4ba5bb9eaf
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

読み込み中…