Potassium Carbonate → 3-(4-Cyanophenoxy)-5-hydroxy benzoic acid ethyl ester

HRID 1024729

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH2:16]([O:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([OH:26])[CH:23]=[C:22]([OH:27])[CH:21]=1)[CH3:17]>CN(C=O)C>[CH2:16]([O:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([OH:26])[CH:23]=[C:22]([O:27][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH:21]=1)[CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

Potassium carbonate 6.7 g (48.5 mmol) followed by 4-fluoro benzonitrile 3.3 g (27.2 mmol) in 10 ml of DMF was added to a solution of 3,5-dihydroxy benzoic acid ethyl ester 5 g (27.4 mmol) in 20 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and was then heated to 45° C. for 10 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated. The crude compound was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 1.15 g of the required product. 1H NMR (DMSO-d6): δ 1.3 (3H, t), 4.3 (2H, q), 6.76 (1H, s), 7.02 (1H, s), 7.36 (2H, d), 7.24 (1H, s), 7.88 (2H, d), 10.3 (1H, s).

Aufarbeitung

customto attain RT
customThe reaction mixture was quenched with ice cold water
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated
customThe crude compound was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-9aa0e02040034d8faf78beceaba2a0c4
Quelldatensatz: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08722930B2

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