2-Naphthol → (+/-)-alpha-(2Naphthyloxymethyl)-3-pyridinepropanol

HRID 1600890Notes

Reaction equation

HRID 1600890 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[H-].[Na+].[O:14]1[CH2:16][CH:15]1[CH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1>CN(C)C=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:16][CH:15]([OH:14])[CH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 24758Sodium hydrideHCID 10877288HCID 10877288, compound

Product 1

HCID 21830672(+/-)-alpha-(2Naphthyloxymethyl)-3-pyridinepropanolYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 5 from 2-naphthol (0.150 g), sodium hydride (0.044 g; 60% dispersion in oil) and (±)-3-(2-oxiranylethyl)pyridine (0.150 g) in dimethylformamide at 100° C. for 30 minutes to give the title compound as a solid (0.050 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4afc97a3c59a49b79a077c9e927afeaa
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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