Benzene → 1-(4-Methoxyphenyl)cyclohexanecarbonitrile

HRID 2375203

反応式

HRID 2375203 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 986291-(4-Methoxyphenyl)cyclohexanecarbonitrile収率 63.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-26ab8c81a5074ccb88c43aedc062d545
出典データセット
uspto-grants-2008_12
特許番号
US07465719B2

関連ノート

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