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

HRID 253255노트

반응식

HRID 253255 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4619461f5b344fdbae0a49b6b7b4042f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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