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

HRID 503227노트

반응식

HRID 503227 반응식
[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

참가 물질

7

반응물 3

HCID 1140Toluene2회HCID 78491-Bromo-2-ChloroethaneHCID 27580313,4-Dibenzyloxyphenylacetonitrile

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2c3aa25e80394fbb8592d8bca45996bc
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776905B2

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