Réaction #68345

Équation de réaction

NaClO2

ethyl3-formyl-2-isopropyl-1-(oxazol-2-ylmethyl)-1H-indole-6-carboxylate

Compound 38

ethyl3-formyl-2-isopropyl-1-(oxazol-2-ylmethyl)-1H-indole-6-carboxylate

→

title compound

6-(Ethoxycarbonyl)-2-isopropyl-1-(oxazol-2-ylmethyl)-1H-indole-3-carboxylic Acid

Solvants

H2O

2-methyl-2-butene

t-BuOH

Conditions de réaction

Traitement

1. 1
   ExtractionThe reaction mixture was extracted with EtOAc (×3)
2. 2
   Lavagethe combined organic layer was washed with brine
3. 3
   Séchagedried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreThe residue was purified by chromatography on silica gel (0→55% EtOAc-hexanes)

Mode opératoire

Following General Procedure D, ethyl3-formyl-2-isopropyl-1-(oxazol-2-ylmethyl)-1H-indole-6-carboxylate (Compound 38, 240 mg, 0.70 mmol) in t-BuOH (20 ml), 2-methyl-2-butene (2.0 ml) was added a solution of NaH2PO4 (1.69 g, 14.0 mmol) and NaClO2 (80%, 1.27 g, 14.0 mmol) in H2O (4 ml). The mixture was stirred at room temperature for 12 h. The reaction mixture was extracted with EtOAc (×3) and the combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→55% EtOAc-hexanes) to yield the title compound as a light tan solid.

Source