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

HRID 720550

反応式

HRID 720550 の反応式
[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]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 1382224-IsopropylphenylacetonitrileHCID 2733832Lithium Hexamethyldisilazide

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-46df4c6e30f74d1a813ac9275cd68f9c
出典データセット
uspto-grants-2006_11
特許番号
US07135487B2

関連ノート

読み込み中…