Water → 4-Ethyl-2-isopropoxy-benzonitrile

HRID 1167309노트

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HRID 1167309 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](I)=[C:5]([O:10][CH:11]([CH3:13])[CH3:12])[CH:4]=1)[CH3:2].O.[CH3:15][N:16](C)C=O>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:15]#[N:16])=[C:5]([O:10][CH:11]([CH3:13])[CH3:12])[CH:4]=1)[CH3:2]

참가 물질

6

반응물 3

HCID 962WaterHCID 6228DimethylformamideHCID 229962054-Ethyl-1-iodo-2-isopropoxy-benzene

생성물 1

HCID 229961874-Ethyl-2-isopropoxy-benzonitrile수율 56%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매

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온도
90 °C

실험 절차

4-Ethyl-1-iodo-2-isopropoxy-benzene (0.93 g, 3.2 mmol) was dissolved in dimethylformamide (5 mL). Zinc cyanide (226 mg, 1.92 mmol) was added. Argon gas was passed through the mixture for 10 min. Tetrakis(triphenylphosphine)-palladium(184 mg, 0.16 mmol) was added and the mixture was heated at 90° C. for 5 h. The reaction mixture was cooled to room temperature and poured into water. The mixture was extracted with diethyl ether. The organic extracts were washed with brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 10% diethyl ether in hexanes yielded 4-ethyl-2-isopropoxy-benzonitrile (0.34 g, 56%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with diethyl ether
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solid was then filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  8. washeluting with 10% diethyl ether in hexanes

출처 및 근거

ORD 기록
ord-cdd3bb24cb5f418f94d1f9c01ceb1f52
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617346B1

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