Methyl iodide → HCID 57544371, 화합물

HRID 537966노트

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HRID 537966 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 57544371HCID 57544371, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f589b786d3b4f268f241abe399fcfee
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865707B2

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