Hydrochloric Acid → (RS)-(2,6-difluoro-4-trifluoromethanesulfonyloxy-phenyl)-ethoxy-acetic acid ethyl ester

HRID 1247373Notizen

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2].[O:19](S(C(F)(F)F)(=O)=O)[S:20]([C:23]([F:26])([F:25])[F:24])(=O)=[O:21].Cl>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:21])=[O:19])=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester (500 mg) in pyridine (5 ml) was placed under N2 and cooled to 0° C. Tf2O (813 mg) was added and the resulting solution was left to stir in the ice bath. After 18 h the reaction mixture was poured on a mixture of 50 ml 1 N HCl and ice. The product was extracted with AcOEt. The organic layer was washed with more 1 N HCl (50 ml), water (50 ml) and brine (30 ml). The aqueous layers were extracted with more AcOEt. After drying (MgSO4) the solvent was evaporated to obtain 738 mg (98%) of (RS)-(2,6-difluoro-4-trifluoromethanesulfonyloxy-phenyl)-ethoxy-acetic acid ethyl ester. Yellow oil. MS 393.4 ([M+H]+).

Aufarbeitung

waitthe resulting solution was left
extractionThe product was extracted with AcOEt
washThe organic layer was washed with more 1 N HCl (50 ml), water (50 ml) and brine (30 ml)
extractionThe aqueous layers were extracted with more AcOEt
dry with materialAfter drying (MgSO4) the solvent
customwas evaporated

Quellen und Nachweise

ORD-Eintrag: ord-4d14dee68f2349f289c201fd70f28d2e
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07129238B2

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