Water → 2-[4-(2-Cyclopentyl-2-oxo-ethoxy)-2-fluoro-phenyl]-2-methyl-propionitrile

HRID 858849ノート

反応式

HRID 858849 の反応式
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[C:15]([CH3:19])([CH3:18])[C:16]#[N:17].Cl[CH2:21][C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23].O>CN(C=O)C>[CH:24]1([C:22](=[O:23])[CH2:21][O:14][C:12]2[CH:11]=[CH:10][C:9]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[C:8]([F:7])[CH:13]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124665772-Chloro-1-cyclopentylethanoneHCID 601250122-(2-Fluoro-4-hydroxyphenyl)-2-methylpropanenitrile

生成物 1

HCID 601250052-[4-(2-Cyclopentyl-2-oxo-ethoxy)-2-fluoro-phenyl]-2-methyl-propionitrile収率 75%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (3.1 g, 22 mmol) was added to a solution of 2-(2-Fluoro-4-hydroxy-phenyl)-2-methyl-propionitrile (1.0 g, 6.0 mmol) and 2-Chloro-1-cyclopentyl-ethanone (3.3 g, 22 mmol) in DMF (20 mL). The mixture was stirred at room temperature for 16 hours. The mixture was poured into water (100 mL) and extracted with EtOAc (2×50 mL). The organics were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (0–15% EtOAc in hexanes) to give the product (1.2 g, 75% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ: 1.57–1.93 (m, 14 H), 3.10 (m, 1 H), 4.64 (s, 2 H), 6.65 (d, J=9.6 Hz, 2 H), 7.37 (t, J=8.9 Hz, 1 H).

後処理

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe organics were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (0–15% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-28e2f29242a04d0dbe2408eb62832e68
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

反応ノート

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