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

HRID 400644

반응식

HRID 400644 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 105113792-Methyl-2-phenylpent-4-enenitrile수율 99.6%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매2회HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-92b51de5a53942ec8f909e4ba5bb9eaf
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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