Reaktion #564688

Reaktionsgleichung

lithium hydroxide

title compound

methyl 3-[7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl]propanoate

→

title compound

Ausbeute 89.1%

3-[7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl]propanoic acid

Ausbeute 89.1%

Lösungsmittel

water

tetrahydrofuran

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was evaporated
2. 2
   workup.ADDITIONwater was added to the residue
3. 3
   ExtraktionAfter extracting with a small amount of diethyl ether
4. 4
   Sonstigeto stand in the cold overnight
5. 5
   FiltrationThe solid was filtered
6. 6
   Waschenwashed with water
7. 7
   Sonstigerecrystallized from ethyl acetate/hexane

Vorschrift

A solution of 0.5 g (19.5 mmole) of lithium hydroxide in 10 ml of water was added to a solution of 2.2 g (3.9 mmole) of the title compound of Example 6 in 25 ml of tetrahydrofuran and 20 ml of methanol. After the reaction mixture was stirred for 3 hours at room temperature, the solvent was evaporated and water was added to the residue. After extracting with a small amount of diethyl ether, the aqueous layer was acidified with dilute hydrochloric acid and allowed to stand in the cold overnight. The solid was filtered, washed with water and recrystallized from ethyl acetate/hexane to yield 1.83 g of the title compound, mp. 80°-83°. Structure assignment was confirmed by nmr and infrared spectra and by elemental analysis.

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