By Richard S. Monson
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Extra info for Advanced Organic Synthesis, Methods and Techniques
29, 955 (1964). Catalytic Hydrogenation The technique of catalytic hydrogenation can be applied almost universally to unsaturated systems, and therein lies its chief advantage (7). By appropriate selection of catalyst, pressure, and temperature, a remarkable variety of substrates can be made to undergo hydrogenation, many of them under hydrogen pressure not exceeding 50 psi (see Appendix 3 for description and use of low-pressure hydrogenation apparatus). A recent development in the technique of hydrogenation has been the use of homogeneous catalysts.
9. W. Huckel and W. Kraus, Chem. Ber. 92, 1158 (1959). Hydroboration A remarkable variation of the hydride reduction is the addition to double bonds of diborane (B2H6) (7). Easily generated by the reaction of boron trifluoride etherate with sodium borohydride, the reagent may be used in the generating solution or may be distilled into a receiving flask containing an ether as solvent. Diborane reacts with unsaturated polar functional groups with results similar to those of the metal hydride reducing agents.
The trialkylborane is oxidized by the addition to the stirred reaction mixture of 32 ml of a 3 TV solution of sodium hydroxide, followed by the dropwise addition of 32 ml of 30 % hydrogen peroxide at a temperature of 30-32° (water bath). The reaction mixture is saturated with sodium chloride and the tetrahydrofuran layer formed is separated and washed with saturated sodium chloride solution. The organic solution is dried over anhydrous magnesium sulfate and the THF is removed. 5 g (80%) of 4-methyl-l-pentanol, bp 151-153°/735 mm.
Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson