Trimethylsilyldiazomethane → Methyl 4-cyano-2-ethoxybenzoate

HRID 2105831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105831
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=1)#[N:9]>C1C=CC=CC=1.CO>[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:16][CH3:1])=[O:15])=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=1)#[N:9]

Komponenten

5

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 226750384-Cyano-2-ethoxybenzoic acid

Produkt 1

HCID 57809105Methyl 4-cyano-2-ethoxybenzoateAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

(Trimethylsilyl)diazomethane (2 M in hexanes, 1.47 mL, 2.93 mmol) was added to a solution of 4-cyano-2-ethoxybenzoic acid (280 mg, 1.47 mmol) in benzene (8.0 mL) and methanol (1.6 mL). The reaction was stirred for 1 h and then degassed with air for 30 min. Evaporation of the solvent and purification of the crude residue by flash column chromatography (silica gel, eluting with 0-20% ethyl acetate in hexanes) gave methyl 4-cyano-2-ethoxybenzoate as a yellow solid (218 mg, 71%).

Aufarbeitung

  1. customdegassed with air for 30 min
  2. customEvaporation of the solvent and purification of the crude residue
  3. washby flash column chromatography (silica gel, eluting with 0-20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-412f143d7b93495ba41db8c247a39c92
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579368B2

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