CYANATION OF ALCOHOLS
1649
(433 mg, 2.71 mmol, 1 equiv.) in 4 mL of anhydrous CH2Cl2. The reaction was
monitored by thin-layer chromatography (TLC; C6H12=CH2Cl2, 3:2) to follow the
formation of the halogenated intermediate (typically 1 h). The flask was then placed
an ice bath, and DBU (415 mL, 1.05 equiv.) was introduced. The mixture was further
stirred at room temperature for 2 h. Solvents were then evaporated under vacuum,
and the resulting brownish oil was chromatographed on silica (C6H12=CH2Cl2, 3:2)
to give 1-naphtylacetonitrile as a colorless oil (329 mg, 69% yield).
Data
1H NMR (CDCl3): d 4.5 (s, 2H), 7.5 (m, 1H), 7.6 (m, 3H), 7.9 (m, 3H). 13C
NMR (CDCl3): d 21.6, 117.6, 122.3, 125.4, 125.7, 126.3, 126.4, 127.0, 128.9, 129.0,
130.7, 133.6. IR (neat): 3051, 2252, 1599, 1511, 1397, 792, 774 cmꢀ1
.
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