Potassium Cyanide → (2-(Methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile

HRID 253255ノート

反応式

HRID 253255 の反応式
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])[C:4]=1[O:14][CH3:15].[C-:16]#[N:17].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:15][O:14][C:4]1[C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][C:16]#[N:17]

参加物

5

反応物 2

HCID 9032Potassium CyanideHCID 668907801-(Chloromethyl)-2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}benzene

生成物 1

HCID 66890258(2-(Methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile収率 54.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

1-(Chloromethyl)-2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}benzene (0.33 g, 1.4 mmol) was dissolved in N,N-dimethylformamide (2 mL) followed by the addition potassium cyanide (0.12 g, 1.6 mmol), and the resulting mixture was heated at 60° C. for 18 hours. After cooling to room temperature, it was diluted with ethyl acetate (50 mL), washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (50% ethyl acetate/hexanes) to provide (2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (0.17 g, 0.76 mmol, 54% yield). 1H NMR (400 MHz, CDCl3): 7.03-7.00 (d, d, 1H), 6.95-6.89 (m, 2H), 4.16-4.14 (m, 2H), 3.94 (s, 3H), 3.79-3.77 (m, 2H), 3.70 (s, 2H), 3.44 (s, 3H).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine (20 mL each)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oily residue which
  7. customwas purified by flash chromatography (50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-4619461f5b344fdbae0a49b6b7b4042f
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

反応ノート

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