Nitromethane → 3-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol

HRID 1627331

Reaktionsgleichung

Reaktionsgleichung von HRID 1627331
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH:12]=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F-].[K+].[CH3:18][N+:19]([O-:21])=[O:20]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH:12]([OH:13])[CH2:18][N+:19]([O-:21])=[O:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 522689Potassium FluorideHCID 592591132-(3,4-Dimethoxyphenyl)-2-methylpropanal

Produkt 1

HCID 667407963-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-olAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(3,4-dimethoxyphenyl)-2-methylpropanal (1.0 g, 4.8 mmol) in EtOH (30 mL) were added KF (335 mg, 5.8 mmol) and CH3NO2 (1.56 mL, 28.8 mmol). The resulting mixture was stirred overnight at room temperature. The solution was concentrated, diluted with EtOAc, and washed with brine. The organic layer was dried over MgSO4, filtered and concentrated to give 3-(3,4-dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol (1.25 g, 97%). 1H NMR (400 MHz, CDCl3) δ 6.91-6.84 (m, 3H), 4.44 (m, 1H), 4.24 (d, 2H), 3.90 (s, 3H), 3.88 (s, 3H), 2.38 (d, 1H), 1.40 (s, 3H), 1.38 (s, 3H).

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f24fcd48f1c94012aebd3d4e53406754
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785488B2

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