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Several decades ago, Wollemberg and Miller developed a useful procedure for the preparation of primary nitroalkanes with an extra atom beginning from aldehydes [37]. The starting point is the nitroaldol (Henry) reaction (Scheme 1.17) of an aldehyde with nitromethane, catalyzed with KF and in the presence of i-PrOH as solvent. The formed nitroalkanol is acetylated (acetic anhydride in the presence of 4-dimethylaminopridine as catalyst) and treated with sodium borohydride affording the desired nitroalkane via “one-pot” acetic acid-elimination and C=C double bond reduction.

So, this procedure offers the opportunity to increase the chain length of the starting aldehyde.

Table 1.3 Reduction of nitroalkenes with NaCNBH₃ (selected examples).

Nitroalkene	Nitroalkane	Yield (%)
		79
		74
		70
		78
		78
		69