반응 #345330

반응 방정식

1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester

4-chlorophenylethyl alcohol

→

1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, 4 -chlorophenylethyl ester

반응 조건

후처리

1. 1
   온도The mixture was gently heated
2. 2
   온도without refluxing for 4 hours
3. 3
   기타The 4-chlorophenylethyl alcohol was removed by distillation under high vacuum
4. 4
   workup.DISSOLUTIONthe crude residue was dissolved in dichloromethane (20 ml)
5. 5
   세척washed successively with two 100 ml portions of saturated ammonium chloride solution, two 100 ml portions of saturated sodium bicarbonate solution and 100 ml of brine
6. 6
   건조The organic phase was dried (Na2SO4)
7. 7
   여과filtered
8. 8
   기타purified
9. 9
   기타the solvent removed under vacuum

실험 절차

To a chilled (0° C.) solution of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, ethyl ester (1.18 g) in 4-chlorophenylethyl alcohol (31 ml) was added titanium (IV) ethoxide (0.30 ml) under a nitrogen atmosphere with stirring. The mixture was gently heated without refluxing for 4 hours. The 4-chlorophenylethyl alcohol was removed by distillation under high vacuum and the crude residue was dissolved in dichloromethane (20 ml) and washed successively with two 100 ml portions of saturated ammonium chloride solution, two 100 ml portions of saturated sodium bicarbonate solution and 100 ml of brine. The organic phase was dried (Na2SO4) filtered, and purified using preparative HPLC (silica gel, 3% methanol in dichloromethane as the loading solvent and eluent). The appropriate fractions were combined and the solvent removed under vacuum. Concentration of the appropriate fractions yielded 0.87 g of 1,2,3,3a,8,8a-hexahydro-α-oxo-1,3a,8-trimethyl-5-pyrrolo[2,3-b]indole acetic acid, 4 -chlorophenylethyl ester as an oil.

출처