Benzene → 1-(4-Methoxyphenyl)cyclohexanecarbonitrile

HRID 2375203

반응식

HRID 2375203 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[H-].[Na+].C1C=CC=CC=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:10]#[N:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 241BenzeneHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 66031Benzeneacetonitrile, 4-methoxy-

생성물 1

HCID 986291-(4-Methoxyphenyl)cyclohexanecarbonitrile수율 63.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-methoxyphenylacetonitrile (E1) (1.002 g, 6.8 mmol) and 1,5-dibromopentane (1.886 g, 8.2 mmol) in dry dimethylformamide (15 ml) at ice bath temperature slowly (ca. 2-3 minutes) a 60% suspension of NaH in mineral oil (0.579 g, 14.4 mmol) was added. The obtained reaction mixture was stirred for 15 minutes at ice bath temperature and for 1.5 hours at room temperature, then the contents were poured into benzene (75 ml). The mixture was successively washed with water (3×75 ml), brine (25 ml), and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with petroleum ether-ethyl acetate (5:1) as eluent to give the title compound (0.924 g, 63%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.00-2.28 (10H, m); 3.81 (3H, s); 6.90 (2H, d, J=9.0 Hz); 7.40 (2H, d, J=9.0 Hz).

후처리

  1. customThe obtained reaction mixture
  2. waitfor 1.5 hours at room temperature
  3. washThe mixture was successively washed with water (3×75 ml), brine (25 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silicagel (50 g) with petroleum ether-ethyl acetate (5:1) as eluent

출처 및 근거

ORD 기록
ord-26ab8c81a5074ccb88c43aedc062d545
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465719B2

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