Methyl iodide → 2-Methyl-2-phenyl-cyclopentanone

HRID 475816

反応式

HRID 475816 の反応式
[H-].[Na+].[C:3]1([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:15]I>COCCOC>[CH3:15][C:9]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:13][CH2:12][CH2:11][C:10]1=[O:14]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2901542-Phenylcyclopentanone

生成物 1

HCID 3499412-Methyl-2-phenyl-cyclopentanone収率 73.9%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a slurry of 60% NaH (125 mg, 3.12 mmol) in DME (3571 μL) at 0° C. was added 2-phenylcyclopentanone (500 mg, 3.12 mmol). After stirring for 1 h, MeI (898 μL, 14.36 mmol) was added, and the solution heated to reflux for 2 h. The reaction was poured onto ice and extracted 3 times into Et2O. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Applied to Silica gel and eluted with an EtOAc/Hex gradient to afford 2-methyl-2-phenylcyclopentanone (401.7 mg, 2.305 mmol, 73.9% yield). LC-MS (M+H)+=175.1. 1H NMR (500 MHz, CDCl3) δ ppm 7.29-7.37 (4H, m), 7.20-7.24 (1H, m), 2.54 (1H, dt, J=12.51, 6.26 Hz), 2.34 (2H, t, J=7.63 Hz), 1.82-2.05 (3H, m), 1.38 (3H, s).

後処理

  1. temperaturethe solution heated
  2. temperatureto reflux for 2 h
  3. additionThe reaction was poured onto ice
  4. extractionextracted 3 times into Et2O
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washApplied to Silica gel and eluted with an EtOAc/Hex gradient

出典と根拠

ORDレコード
ord-ade240b11c6345c3b092b156bd30b922
出典データセット
uspto-grants-2014_01
特許番号
US08637525B2

関連ノート

読み込み中…