Reaktion #1835747

Reaktionsgleichung

4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid methyl ester

sodium hydroxide

→

4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid

Ausbeute 59.2%

Lösungsmittel

tetrahydrofuran

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   Sonstigethe organic solvent was evaporated
3. 3
   workup.ADDITIONdiluted with 1 N aqueous solution of sodium hydroxide and water, diethyl ether
4. 4
   workup.ADDITIONwas added
5. 5
   Sonstigethe aqueous layer was separated
6. 6
   Temperaturcooled
7. 7
   workup.ADDITIONconcentrated hydrochloric acid was added
8. 8
   Extraktionextracted with chloroform
9. 9
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
10. 10
    Sonstigethe solvent was evaporated

Vorschrift

To a solution of 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid methyl ester (745 mg) in tetrahydrofuran (5 ml) and methanol (5 ml) was added 4 N aqueous solution of sodium hydroxide (5 ml) at room temperature, and stirred overnight. After completion of the reaction, the organic solvent was evaporated, diluted with 1 N aqueous solution of sodium hydroxide and water, diethyl ether was added thereto, and the aqueous layer was separated. The aqueous layer was ice-cooled, concentrated hydrochloric acid was added thereto to adjust the layer to pH 4, extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid (421 mg) as a white solid. MS (ESI) m/z: 300, 302 (M+H)+.

Quelle