Methyl iodide → HCID 57544371、化合物

HRID 537966ノート

反応式

HRID 537966 の反応式
[O-][CH2:2]C.[Na+].[F:5][C:6]([F:23])([F:22])[C:7]1[CH:8]=[C:9]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[C:10]([CH2:12][C:13]#[N:14])=[O:11].CI>CCO>[F:5][C:6]([F:22])([F:23])[C:7]1[CH:8]=[C:9]([C:10](=[O:11])[CH:12]([CH3:2])[C:13]#[N:14])[CH:15]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:17]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 247268153,5-Bis(Trifluoromethyl)Benzoylacetonitrile

生成物 1

HCID 57544371HCID 57544371、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of sodium ethoxide (0.127 g, 1.87 mmol) in EtOH (5 mL) was treated with 3,5-bis(trifluoromethyl)benzoyl acetonitrile (0.500 g, 1.78 mmol) portionwise over 5 min. The reaction was heated at reflux for 30 min before the addition of methyl iodide (0.41 mL, 6.6 mmol). Heating at reflux was continued for a further 2 h before the reaction mixture was allowed to cool and concentrated in vacuo. The residue was partitioned between H2O (10 mL) and EtOAC (20 mL) and the aqueous phase was separated and re-extracted with EtOAC (2×20 mL). The combined organic extracts were washed with brine (25 mL), dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography on silica gel (0-20% EtOAc in hexanes gradient) to afford 3-[3,5-bis(trifluoromethyl)phenyl]-2-methyl-3-oxopropanenitrile. 1H NMR (500 MHz, CDCl3) δ 8.21 (s, 2H), 8.10 (s, 1H), 4.42 (q, J=7.1 Hz, 1H), 1.71 (d, J=7.1 Hz, 6H).

後処理

  1. temperatureThe reaction was heated
  2. temperatureHeating
  3. temperatureat reflux
  4. temperatureto cool
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between H2O (10 mL) and EtOAC (20 mL)
  7. customthe aqueous phase was separated
  8. extractionre-extracted with EtOAC (2×20 mL)
  9. washThe combined organic extracts were washed with brine (25 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product was purified by flash chromatography on silica gel (0-20% EtOAc in hexanes gradient)

出典と根拠

ORDレコード
ord-7f589b786d3b4f268f241abe399fcfee
出典データセット
uspto-grants-2014_10
特許番号
US08865707B2

反応ノート

読み込み中…