Ethanol → 2-(2,5-Difluoro-4-nitro-phenyl)-4-methyl-pentanoic acid ethyl ester

HRID 1183588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183588
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[CH:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14].OS(O)(=O)=O.[CH3:25][CH2:26]O>>[CH2:25]([O:14][C:13](=[O:15])[CH:12]([C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:26]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 579955592-(2,5-Difluoro-4-nitro-phenyl)-4-methyl-pentanoic acid

Produkt 1

HCID 579956072-(2,5-Difluoro-4-nitro-phenyl)-4-methyl-pentanoic acid ethyl ester

Versuchsvorschrift

2-(2,5-difluoro-4-nitro-phenyl)-4-methyl-pentanoic acid (29.0 g, 0.11 mol) was dissolved in EtOH (200 mL) and H2SO4 (96%) 10 mL added. The reaction mixture was refluxed for 3 h and the solvent evaporated to an oil which was dissolved in EtOAc. Water (150 mL) added and the reaction mixture was extracted with EtOAc (3×100 mL). Organic phases washed with saturated NaHCO3 (50 mL), water (100 mL) and brine (100 mL) then dried under MgSO4. The evaporation of solvent under reduced pressure gave 2-(2,5-difluoro-4-nitro-phenyl)-4-methyl-pentanoic acid ethyl ester as yellow oil 32.0 g, (97%), which was used for the next step without purification. 1H NMR (300 MHz, CDCl3/TMS): δ 7.81 (dd, J=8.8, 6.2 Hz, 1H), 7.41 (dd, J=11.1, 5.6 Hz, 1H), 4.23-4.05 (m, 3H), 2.04-1.94 (m, 1H), 1.71-1.62 (m, 1H), 1.51-1.42 (m, 1H), 1.25 (t, J=7.1 Hz, 3H), 0.95-0.92 (m, 6H); 13C NMR (75 MHz, CDCl3/TMS): δ 171.6, 155.0 (d, 1JCF=246.0 Hz), 151.5 (d, 1JCF=261.3 Hz), 145.5, 135.7, 118.8 (dd, 2JCF=24.0, 3JCF=4.0 Hz), 113.0 (d, 2JCF=20.0 Hz), 61.6, 41.8, 26.1, 22.5, 22.0, 14.1.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customthe solvent evaporated to an oil which
  3. dissolutionwas dissolved in EtOAc
  4. additionWater (150 mL) added
  5. extractionthe reaction mixture was extracted with EtOAc (3×100 mL)
  6. washOrganic phases washed with saturated NaHCO3 (50 mL), water (100 mL) and brine (100 mL)
  7. customthen dried under MgSO4
  8. customThe evaporation of solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d906cfbd46e84ee8bbaa5eeeef93fd15
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664249B2

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