Potassium Carbonate → Methyl 3-cyano-4-isopropoxybenzoate

HRID 1785066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785066
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].C([O-])([O-])=O.[K+].[K+].C(C(N)CBr)(O[C:23](C)([CH3:25])[CH3:24])=O>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:23]([CH3:25])[CH3:24])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11769089Methyl 3-cyano-4-hydroxybenzoateHCID 22273677Boc-aminoethyl bromide

Produkt 1

HCID 21956805Methyl 3-cyano-4-isopropoxybenzoateAusbeute 109,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of compound 3 (5.000 g, 17 mmol) in DMF (15 mL) was added K2CO3 (3.51 g, 26 mmol) and Boc-2-amino ethyl bromide (4.56 g, 20.35 mmol). The resulting mixture was stirred at 60° C. for three hours. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4 and concentrated. Purification with column chromatography (Hexanes/EtOAc 50:50) gave the product 4 (4.08 g, 55%) as white solid.

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification with column chromatography (Hexanes/EtOAc 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-b50a8b6695f44fe6b0f3f331f83d2e58
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504413B2

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