1,2,3,4-Tetrahydro-1-naphthalenol → 2-Chloro-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridine

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Reaction Steps

Using the method of Example 3, Step A, 1,2,3,4-tetrahydronaphthalen-1-ol (935 mg, 6.31 mmol), 60% sodium hydride in mineral oil (252 mg, 6.31 mmol), and 2-chloro-4-nitropyridine (1.00 g, 6.31 mmol) were reacted to provide 2-chloro-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridine (1.62 g, 99% yield) as an oil. 1H NMR (CDCl3) δ 8.21 (d, 1H), 7.17-7.30 (m, 4H), 6.95 (s, 1H), 6.83 (d, 1H), 5.46 (t, 1H), 2.89 (ddd, 1H), 2.80 (ddd, 1H), 2.17 (m, 1H), 2.06 (m, 1H), 1.97 (m, 1H), 1.84 (m, 1H).

Provenance & Evidence