Methyl iodide → 2-[4-(Propan-2-yl)phenyl]propanenitrile

HRID 380959

반응식

HRID 380959 반응식
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:13][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>O1CCCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 1382224-IsopropylphenylacetonitrileHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 136820102-[4-(Propan-2-yl)phenyl]propanenitrile수율 73%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

In a 250 ml flask, 4-isopropylphenylacetonitrile 8.00 g (50.2 mmol) was dissolved in tetrahydrofuran (150 ml) under a nitrogen atmosphere. The solution was cooled to −78° C. and lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 52.8 ml (52.8 mmol) added. The resulting mixture was stirred at −78° C. for 1 hour. To this reaction mixture was added iodomethane 3.29 ml (52.8 mmol). The resulting mixture was slowly allowed to warm to ambient temperature over 16 hours then quenched with 0.2M hydrochloric acid and extracted twice with diethyl ether. The organic fractions were combined, dried (MgSO4) and concentrated under vacuo. Chromatography (SiO2, 20% ethyl acetate/hexanes) gave 6.32 g (73%) of the title compound.

후처리

  1. temperatureto warm to ambient temperature over 16 hours
  2. customthen quenched with 0.2M hydrochloric acid
  3. extractionextracted twice with diethyl ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuo

출처 및 근거

ORD 기록
ord-793116bc8cc54d469787254f6d747cbb
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303816B1

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