Ciba-Geigy Limited, Pharmaceuticals Division, CH-4002 Basel, Switzerland
*Present Address: Molecular Diversity Preservation International (MDPI), Saengergasse 25, CH-4054 Basel, Switzerland. Tel. +41 79 322 3379, Fax +41 61 302 8918, E-mail: [email protected]
With biographical summary
Received: 7 July 1997 / Uploaded: 23 July 1997
Abstract: The preparation and spectroscopic characterization of 1,3-di(4-benzyloxybenzoyl)indole is reported in this communication.
Keywords: Indole, 1,3-di(4-benzyloxybenzoyl)indole.
Introduction
1,3-Di(4-benzyloxybenzoyl)indole is an interesting compound (This is a sample paragraph) [1].
1,3-Di(4-benzyloxybenzoyl)indole is an interesting compounds (This is a sample paragraph).
As shown in the scheme, this reaction is interesting. (This is a sample paragraph)
We prepared 1,3-di(4-benzyloxybenzoyl)indole. The yield is very low and we will improve it, if necessary. (This is a sample paragraph).
Experimental Part
1,3-Di(4-benzyloxybenzoyl)indole is an interesting compounds (This is a sample paragraph).
The general part of the experimental section [2] 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.
Acknowledgments: The author would like to thank Dr. Vittorio Rasetti for
his support.
References and Notes
1. The preliminary results were published in the MolBank column of Molecules: Lin, S. -K.
1,3-Di(4-benzyloxybenzoyl)indole. Molecules
2. 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.
Sample Availability: Available from MDPI, 0.1745g, MDPI 9940.
Shu-Kun born March 24, 1957 in Hanchuan, Hubei Province, China. He graduated from
Wuhan University
in 1982, majoring inorganic chemistry. He studied physical chemistry in the Chinese Academy of Sciences (1982-1986, MSc in 1985) and in the USA (1.1987-7.1989). He obtained his doctorate in organic chemistry at the Swiss Federal Institute of Technology (ETH-Z�rich) in 1992 after three years studies at the group of Prof. Dr. Bernhard Jaun, Lab. f. org. Chemie-ETH-Z�rich. He then worked at Ciba-Geigy Ltd. for ca. three years, first as a postdoctoral research associate in organic synthesis and worked on two drug discovery programmes in CNS area for 1.5 years, then worked at the Dyestuffs Division of Ciba-Geigy Ltd. and received training in dyestuff R&D and production. He initiated a molecular diversity preservation project and founded MDPI (Molecular Diversity Preservation International), a nonprofit and independent international organization in Switzerland. In 1995 he launched the first journal Molecules that encourages authors to deposit their compound samples. He is the main author of 40 publications. He has two children (a daughter Qian-Qian, born July 27, 1986, and a son, Di-Fan, born June 1, 1996). His personal website is http://www.mdpi.org/lin.htm. Present Address: Dr. Shu-Kun Lin, Molecular Diversity Preservation International (MDPI), Saengergasse 25, CH-4054 Basel, Switzerland. Tel. +41 79 322 3379, Fax +41 61 302 8918, E-mail: [email protected].