Dimethylformamide → 1-(2,2-Dimethoxyethyl)-3-methyl-2-nitrobenzene

HRID 751481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751481
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:11])([O-:3])=[O:2].[CH3:12][O:13][CH:14]([O:18][CH3:19])N(C)C.CN(C)C=O.C[Si](Cl)(C)C>C(OCC)(=O)C.CO>[CH3:12][O:13][CH:14]([O:18][CH3:19])[CH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:4]=1[N+:1]([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 66722,6-DimethylnitrobenzeneHCID 78373Dimethylformamide dimethyl acetal

Produkt 1

HCID 692699561-(2,2-Dimethoxyethyl)-3-methyl-2-nitrobenzeneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Combine 2-nitro-meta-xylene (5 mL, 0.037 mol), N,N-dimethylformamide dimethylacetal (5.4 mL, 1.1 eq) and N,N-dimethylformamide (60 mL) in a flask and reflux under nitrogen for 2 days. Let cool to room temperature then concentrate to approximately one-half volume. Add methanol (40 mL) and trimethylsilylchloride (6.6 mL, 1.4 eq). Reflux overnight. Dilute with ethyl acetate after cooling to room temperature then extract with saturated sodium bicarbonate followed by brine. Dry over magnesium sulfate, filter and concentrate. Purification by column chromatography (9:1 Hexanes:ethyl acetate) gives 1.15 g (14%) product as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 2.23 (s, 3H), 2.80 (d, J=5.36 Hz, 2H), 3.19 (s, 6H), 4.45 (m, 1H), 7.32 (m, 2H), 7.42 (m, 1H).

Aufarbeitung

  1. concentrationthen concentrate to approximately one-half volume
  2. temperatureReflux overnight
  3. temperatureafter cooling to room temperature
  4. extractionthen extract with saturated sodium bicarbonate
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurification by column chromatography (9:1 Hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b2c7e790db074372a74aaf68d083ad01
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405305B2

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