Sodium hydride → HCID 86634719, compound

HRID 910919Notes

Reaction equation

HRID 910919 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH: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][C:1]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[CH:4]=[CH:3][CH:2]=2)[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 86634719HCID 86634719, compoundYield 98%

Procedure

Using the method of Example 3, Step A, 5,6,7,8-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-(5,6,7,8-tetrahydronaphthalen-1-yloxy)pyridine (1.60 g, 98% yield) as an oil. 1H NMR (CDCl3) δ 8.19 (d, 1H), 7.15 (t, 1H), 7.03 (d, 1H), 6.82 (d, 1H), 6.71-6.75 (m, 2H), 2.82 (t, 2H), 2.52 (t, 2H), 1.71-1.81 (m, 4H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a76d661ad4db45b2a803f32309b2799c
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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