Reaktion #507985

Reaktionsgleichung

1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester

Compound 1

1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester

dihydropyran

p-TsOH

→

1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxylic acid, ethyl ester

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooling bath was removed
2. 2
   SonstigeThe reaction was quenched
3. 3
   workup.ADDITIONby adding aqueous NaHCO3 (20 mL) and CH2Cl2 (50 mL)
4. 4
   SonstigeThe layers were separated
5. 5
   Waschenthe organic layer was washed with brine (20 mL)
6. 6
   Trocknendried (MgSO4), and solvent
7. 7
   Sonstigeremoved under vacuum
8. 8
   SonstigeThe crude mixture was purified by silica gel flash chromatography
9. 9
   Waschenby eluting with 10% EtOAc in hexanes

Vorschrift

To a cold (0° C.) solution of 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 1, 2.3 gm, 6.82 mmol) in CH2Cl2 (31 mL) was added dihydropyran (DHP, 3.1 g, 36.9 mmol) and p-TsOH (50 mg). The cooling bath was removed, and the solution was stirred at ambient temperature for 16 h. The reaction was quenched by adding aqueous NaHCO3 (20 mL) and CH2Cl2 (50 mL). The layers were separated, and the organic layer was washed with brine (20 mL), and dried (MgSO4), and solvent removed under vacuum. The crude mixture was purified by silica gel flash chromatography by eluting with 10% EtOAc in hexanes to isolate 1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxylic acid, ethyl ester (Compound 11) as a thick pale yellow oil.

Quelle