The general part of the experimental section [1] has been presented elsewhere. A stirred solution of indole (3.039g, 25.94mmol) in diethyl ether (40ml) was treated dropwise with methylmagnesium iodide solution [freshly prepared by addition of a solution of methyl iodide (1.65ml, 25.9mmol) in diethyl ether (10ml) to Mg (0.6307g, 25.94mmol) in diethyl ether (5ml)] at 0deg.C and stirred for 1.5 hr after removal of the ice/water bath. The final temperature was 22deg.C. A solution of 4-benzyloxybenzoyl chloride (6.40g, 25.94mmol) in 50ml THF was quickly added without delay. Stirring was then continued at 22deg.C for 1hr. The reaction mixture was poured into a mixture of water (250ml), HCl (1N, 22ml) and ice (50g). NaOH (2N, ca. 10ml) was added to give pH 7. Extraction with ethyl acetate (10 times 80ml) was followed by evaporation and filtration to yield 3.515 g (50.4%) of the title compound, a white powder.
M.p. 180-181deg.C.
TLC (Hexane/EtOAc 1:1): Rf 0.67.
1H-NMR (CDCl3): 8.25 (m, 2H); 7.75-7.90 (m, 5H); 7.42 (m, 12H); 7.08 (m, 4H); 5.17 (d, 4H).
Anal. calc. for C36H27NO4 (537.61): C 80.43, H 5.06, N 2.61; found: C 80.04, H 5.18, N 2.57.
Supplementary materials
Supplementary File 1Supplementary File 2Acknowledgments
The author would like to thank Dr. Vittorio Rasetti for his support.
References and Notes
- Lin, S.-K.; Rasetti, V. Synthesis of benzospiro[5,6]undecane derivatives as inhibitors of steroid 5-a-reductase. Helv. Chim. Acta. 1995, 78, 857–865. [Google Scholar] [CrossRef]
- Sample Availability: Available from MDPI, 0.1745g, MDPI 9940.
© 1997 MDPI. All rights reserved