Benzyl Alcohol → 2-(Benzyloxy)-6-chloropyridine

HRID 1492370Notes

Reaction equation

HRID 1492370 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Cl)[N:11]=1>[H-].[Na+].CN(C)C=O>[CH2:1]([O:8][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([Cl:9])[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 169892,6-Dichloropyridine

Product 1

HCID 112644642-(Benzyloxy)-6-chloropyridineYield 60.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent2×

Procedure

Following the procedure of Example 4a) above, benzyl alcohol (5 g; 46 mmols) reacted with sodium hydride (1.19 g), was refluxed for 1 hour with 2,6-dichloropyridine (6.9 g; 46 mmols) using sodium hydride and dry dimethylformamide as solvent. 2-Benzyloxy-6-chloropyridine (6.1 g; 60%) was obtained as a colorless oil following solvent extraction with chloroform/water (500 ml; 50/50), purification and chromatographic separation of the product from the organic layer, identified by elemental analysis and mass spectrum.

Sources & evidence

ORD record
ord-605037c9f081443487be4d920d5a58ec
Source dataset
uspto-grants-1994_12
Patent number
US05374604

Reaction notes

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