Advanced Organic Synthesis - download pdf or read online

By Richard S. Monson

ISBN-10: 0125049501

ISBN-13: 9780125049504

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The filtrate is concentrated under reduced pressure (rotary evaporator or steam bath), and the residue is dissolved in 25 ml of chloroform. The chloroform solution is washed twice with 10-ml portions of water and twice with 10-ml portions of sodium bicarbonate solution, and finally, dried over anhydrous magnesium sulfate and Norit. The solution is filtered and the solvent is evaporated under vacuum. Treatment of the residue with excess ether gives the crystalline product, which is collected and dried in air.

Finally, water (10 ml) is added to decompose the excess hydride. The alkylborane is oxidized by the addition of 32 ml of 3 TV sodium hydroxide followed by 32 ml of 30 % hydrogen peroxide to the stirred solution maintained at 30-50° (water bath), and the stirring is continued at the temperature for 1 hour. The mixture is extracted three times with 100-ml portions of ether, and the combined extracts are washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. 6°. II.

Winkelmann in "Newer Methods of Preparative Organic Chemistry" ( W. ), Vol. 3, Academic Press, New York, 1964. 8. N. S. Isaacs, "Experiments in Physical Organic Chemistry," p. 276. Macmillan, London, 1969. 9. F. L. Greenwood and M. D. Kellert, /. Amer. Chem. Soc. 75, 4842 (1953); F. L. Greenwood, M. D. Kellert, and J. Sedlak, Org. Syn. Collective Vol. 4, 108 (1963). 10. H. J. Dauben and L. L. McCoy, /. Amer. Chem. Soc. 81, 5405 (1959). 11. H. O. House and H. W. Thompson, /. Org. Chem. 28, 360 (1963).

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Advanced Organic Synthesis by Richard S. Monson


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