Reaktion #42306

Reaktionsgleichung

potassium hydroxide

methyl 3-[(dipropylamino)carbonyl]-5-ethynylbenzoate

→

3-[(dipropylamino)carbonyl]-5-ethynylbenzoic acid

Lösungsmittel

water

chloroform

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   Sonstigethe phases are separated
3. 3
   Einengenthe organic phase is concentrated under reduced pressure

Vorschrift

To a stirred mixture of the protected methyl 3-[(dipropylamino)carbonyl]-5-ethynylbenzoate (XXXII, Step 1, 185.3 mg, 0.49 mmol) in methanol (2.5 mL) is added a mixture of potassium hydroxide (2.9 mL of a 1 M mixture in water, 2.9 mmol). The reaction mixture is stirred for 4 hours diluted with chloroform (40 mL), the phases are separated and the organic phase is concentrated under reduced pressure to give 3-[(dipropylamino)carbonyl]-5-ethynylbenzoic acid, NMR (300 MHz, CDCl3): δ 8.22, 8.05, 7.71, 3.48, 3.17, 3.16, 1.71, 1.55, 1.00 and 0.78.

Quelle