Benzene → 7-Methoxy-3,4-dihydronaphthalene-1-carbonitrile

HRID 1830668노트

반응식

HRID 1830668 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=O)=[CH:5][CH:4]=1.C1C=CC=CC=1.C[Si]([C:24]#[N:25])(C)C.P(Cl)(Cl)(Cl)=O>[I-].[Zn+2].[I-].N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[C:24]#[N:25])=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 241BenzeneHCID 24813Phosphorus oxychlorideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 82115Trimethylsilyl cyanide

생성물 1

HCID 115212017-Methoxy-3,4-dihydronaphthalene-1-carbonitrile

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 1049Pyridine용매

실험 절차

To a mixture of 7-methoxy-1-tetralone (39.65 g, 0.23 mol), zinc iodide (1.73 g, 5.4 mmol), and benzene (100 mLs) was added trimethylsilylcyanide (25.0 g. 0.25 mol). The mixture was stirred overnight at room temperature. Pyridine (350 mL) was added and phosphorous oxychloride (100 mL) was then added dropwise, with a slight temperature increase. The mixture was heated to reflux and held for 6 hr. TLC showed one mid-Rf spot for the desired product. The mixture was stirred overnight at room temperature. The mixture was carefully poured onto ice/hydrochloric acid (about 1.5 liter of 10% HCl). The total volume was 2 liters. This mixture was extracted with ethyl acetate (3×500 mLs), the organics combined and washed with water (2×500 mLs) and then brine (500 mLs). The ethyl acetate was dried over magnesium sulfate and evaporated off provide a liquid which on standing solidified. This crude solid was slurried in hexane and filtered to give 31.3 g (74%) of a tan solid. Some of this material, was purified by silica gel chromatography (10% ethyl acetate-hexanes) to provide a solid: mp 47–49° C.; 1H NMR (DMSO-d6): δ 2.44–2.50 (2H, m), 2.72 (2H, t, J=8.4 Hz), 6.81 (1 H, d, J=2.6 Hz), 6.90 (1H, dd, J=2.9 Hz, J=8.2 Hz), 7.17–7.19 (2H, m); MS m/z 168 ([M−H]−);

후처리

  1. temperatureincrease
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. waitheld for 6 hr

출처 및 근거

ORD 기록
ord-9f3126ebd6c645608470e3090bd20eda
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067524B2

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