1- Nitrobutane, reduction with sodium

This procedure describes the preparation of 3-nitropropanai, 1, employing the rarely encountered 1,4-addition of ambident nitrite ion with its "softer N-atom,2 and further transformations of 1, as reported earlier.3 A similar preparation of 3-nitrobutanal from crotonaldehyde (3-butenal) is known,4 as well as analogous additions to a, 3-enones.2 The reduction of 1 to the alcohol 2, originally carried out with borane-dimethyl sulfide (BMS),3 is now more conveniently and economically done with sodium borohydride. The acetalization of 1 to yield the dimethyl acetal 3 is based on our earlier report.3... 

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