Sodium hydride → (+/-)-alpha-(1-Naphthylthiomethyl)-3-pyridinepropanol

HRID 1600889Notes

Reaction equation

HRID 1600889 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([SH:11])[C:4]2=[CH:3][CH:2]=1.[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>[C:10]1([S:11][CH2:16][CH:15]([OH:14])[CH2:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 682591-NaphthalenethiolHCID 10877288HCID 10877288, compound

Product 1

HCID 21830653(+/-)-alpha-(1-Naphthylthiomethyl)-3-pyridinepropanolYield 34.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 1 from 1-thionaphthol (0.150 g), sodium hydride (0.044 g) and (±)-3-(2-oxiranylethyl)pyridine (0.150 g) in dimethylformamide (3 ml) at room temperature to give the title compound as an oil (0.100 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-806323bc691e48b2992ece19e7b38033
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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