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

HRID 910921Notes

Reaction equation

HRID 910921 reaction equation
[CH:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([N+]([O-])=O)[CH:18]=[CH:17][N:16]=1>>[Cl:14][C:15]1[CH:20]=[C:19]([O:11][CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 107231,2,3,4-Tetrahydro-1-naphthalenolHCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 637781082-Chloro-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridineYield 99%

Procedure

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).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-acde14ccaa53483e8e029fa7839adb6e
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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