Diisopropylethylamine → 5-Tert-butyl-2-methoxy-3-nitrobenzonitrile

HRID 735799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735799
[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:3])[CH3:2].[CH:17](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>CO.C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([O:13][CH3:17])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 589806535-Tert-butyl-2-hydroxyl-3-nitro-benzonitrile

Produkt 1

HCID 508831995-Tert-butyl-2-methoxy-3-nitrobenzonitrileAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21959252Acetonitrile methanolLösungsmittel

Versuchsvorschrift

The above nitrile (0.5 g, 2.27 mmol) was taken up in 1:9 methanol/acetonitrile (20 mL). N,N-diisopropylethylamine (1.1 mL, 6.35 mmol) was added dropwise followed by (trimethylsilyl)diazomethane (3.2 mL, 6.35 mmol). The reaction was stirred until the bubbling stopped (20 min) and the reaction was quenched with water. The water was extracted 3× with methylene chloride, dried over Na2SO4, filtered, and concentrated in vacuo to give 5-tert-butyl-2-methoxy-3-nitro-benzonitrile (0.531 g, 99%) as a yellow solid.

Aufarbeitung

  1. custom(20 min)
  2. customthe reaction was quenched with water
  3. extractionThe water was extracted 3× with methylene chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-849f861350ba48708559e41fb9aaf381
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592332B2

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