Toluene → 1-(3,4-Bis-benzyloxy-phenyl)-cyclopropanecarbonitrile

HRID 468234ノート

反応式

HRID 468234 の反応式
[C:1]1(C)C=CC=C[CH:2]=1.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([CH2:30][C:31]#[N:32])[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.BrCCCl>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].[OH-].[Na+].O>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([C:30]2([C:31]#[N:32])[CH2:2][CH2:1]2)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

7

反応物 3

HCID 1140Toluene2 回HCID 78491-Bromo-2-ChloroethaneHCID 27580313,4-Dibenzyloxyphenylacetonitrile

生成物 1

HCID 670439871-(3,4-Bis-benzyloxy-phenyl)-cyclopropanecarbonitrile収率 66%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
50 °C

実験手順

To a mixture of (n-C4H9)4NBr (0.50 g, 1.5 mmol), toluene (7 mL) and (3,4-bis-benzyloxy-phenyl)-acetonitrile (14 g, 42 mmol) in NaOH (50 g) and H2O (50 mL) was added BrCH2CH2Cl (30 g, 0.21 mol). The reaction mixture was stirred at 50° C. for 5 h before being cooled to room temperature. Toluene (30 mL) was added and the organic layer was separated and washed with H2O, brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1) to give 1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile (10 g, 66%). 1H NMR (DMSO 300 MHz) δ 7.46-7.30 (m, 10H), 7.03 (d, J=8.4 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 6.89 (dd, J=2.4, 8.4 Hz, 1H), 5.12 (d, J=7.5 Hz, 4H), 1.66-1.62 (m, 2H), 1.42-1.37 (m, 2H).

後処理

  1. temperaturebefore being cooled to room temperature
  2. customthe organic layer was separated
  3. washwashed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1)

出典と根拠

ORDレコード
ord-74f87dbfe3ac4840b7af41a9009df302
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

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