Water → 2-{[1-Bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

HRID 1359195노트

반응식

HRID 1359195 반응식
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13]1[O:14][C:15]3[CH:27]=[CH:26][CH:25]=[CH:24][C:16]=3[C:17]=1[C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:35][C:36]#[N:37].O>CC(C)=O>[Br:1][C:2]1[C:3]2[C:8](=[CH:7][C:6]([C:13]3[O:14][C:15]4[CH:27]=[CH:26][CH:25]=[CH:24][C:16]=4[C:17]=3[C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:5][CH:4]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:35][C:36]#[N:37]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 113846851-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

생성물 1

HCID 114198352-{[1-Bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile수율 62%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

The mixture of 1-[2-(5-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (1.46 g, 3.45 mmol) and cesium carbonate (2.36 g, 7.23 mmol) in acetone (16 mL) was stirred at room temperature for 15 minutes. Bromoacetonitrile (0.50 mL, 7.2 mmol) was then added and the mixture was stirred for 4 hours at room temperature then poured into excess water and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by flash chromatography (Biotage apparatus) using 5-20% tert-butyl methyl ether in hexane as an eluant to afford 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy} acetonitrile as a yellow solid (0.989 g), mp 100-102° C. Mass spectrum (−ESI, [M−H]−) m/z 460. 1HNMR (400 MHz, DMSO-d6): δ8.55 (d, 1H, J=0.98 Hz), 8.25 (d, 2H, J=9.3 Hz), 8.0-8.05 (m, 2H), 7.7-7.75 (m, 2H), 7.4-7.5 (m, 2H), 5.5 (s, 2H), 2.75 (t, 2H, J=7.2 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.2 Hz). Elemental Analysis for C25H20BrNO3: Calculated: C, 64.95; H, 4.36; N, 3.03. Found: C, 64.71; H, 4.32; N, 2.86.

후처리

  1. stirringthe mixture was stirred for 4 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customThe residue was purified by flash chromatography (Biotage apparatus)

출처 및 근거

ORD 기록
ord-948ccc65435f49bbb7a00bd2de6396ee
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599925B2

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