Potassium Hydroxide → 3-[(4-Fluorophenyl)thio]-2-hydroxy-2-methylpropanoic acid

HRID 1582777

Reaktionsgleichung

Reaktionsgleichung von HRID 1582777
FC1C=CC(S)=CC=1.[H-].[Na+].[OH:11][C:12]([CH3:26])([CH2:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:13]([O:15]C)=[O:14].[OH-].[K+]>C(O)C>[OH:11][C:12]([CH3:26])([CH2:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:13]([OH:15])=[O:14]

Komponenten

6

Edukt 4

HCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 21966928Methyl 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionate

Produkt 1

HCID 98133673-[(4-Fluorophenyl)thio]-2-hydroxy-2-methylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The methyl 2-methyl-oxirane-carboxylate of formula (1), which was obtained by epoxidation, was reacted with 4-fluorothiophenol [formula (2)] in the presence of sodium hydride under the conditions listed in Scheme-2. The obtained methyl 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionate of formula (3) was hydrolyzed with potassium hydroxide in aqueous ethanol over a period of 22 hours to yield the 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionic acid of formula (4), which was converted into the acid chloride of formula (5) with thionyl chloride in dimethyl acetamide at −15° C.

Quellen und Nachweise

ORD-Eintrag
ord-3fa5eb32fff840078241cabc76813c00
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06737550B2

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