Advanced organic synthesis: methods and techniques by Richard S. Monson

By Richard S. Monson

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C 5 H n -CH 2 ) 3 B * Diethylene glycol dimethyl ether, bp 162°. -^+ (CH 3 ) 2 CHCH 2 CH 2 CH 2 -OH I. HYDROBORATION OF OLEFINS AS A ROUTE TO ALCOHOLS 33 A 500-ml three-necked flask is fitted with a dropping funnel, a condenser, and a magnetic stirrer. 30 mole) of 4-methyl-l-pentene. 12 mole) of boron trifluoride etherate in 20 ml of THF is added over a period of 1 hour, the temperature being maintained at 25° (water bath). The flask is stirred an additional hour at 25° and the excess hydride is decomposed with water (10 ml).

P. von R. Schleyer, M. M. Donaldson, R. D. Nicholas, and C. Cupas, Org. Syn. 42, 8 (1962). 3. J. C. Sircar and A. I. Meyers, /. Org. Chem. 30, 3206 (1965). 4. D. S. Noyce, G. L. Woo, and B. R. Thomas, /. Org. Chem. 25, 260 (1960). 5. W. M. Pearlman, Org. Syn. 49, 75 (1969). 6. J. A. Osborn, F. H. Jardine, J. F. Young, and G. Wilkinson, /. Chem. Soc. (A)1 p. 1711 (1966). 7. A. J. Birch and K. A. M. Walker, /. Chem. Soc. (C), p. 1894 (1966). 8. J. A. Osborn and G. Wilkinson, Inorg. Syn. 10, 67 (1967).

Treatment of 1-hexene with BMB, for example, gives after oxidation, 99% 1-hexanol and 1 % 2-hexanol. Moreover, BMB is found to react only very slowly with di- or trisubstituted olefins, and can therefore be conveniently used as a selective hydroborating agent in the case of variously substituted polyenes. The generation and use of the reagent are described in the procedures. 36 4. HYDROBORATION A. n-OCTANAL FROM 1-OCTYNE (J) (CH3)2C=CHCH3 B2H6 > (iso-C 5 H n ) 2 BH C6H13C=CH +(ISo-C 5 Hn) 2 BH -* C6H13-CH=CH-B(iso-C5Hn)2 2 2 > NaOH «-C 7 H, 5 —CHO + iso-C 5 H n —OH A 500-mI three-necked flask is fitted with a condenser, a pressure-equalizing dropping funnel, a magnetic stirrer, and a thermometer.

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