4,4'-Dihydroxydiphenyl ether → (+/-)-alpha-(4-(4-Hydroxyphenoxy)phenoxymethyl)-3-pyridinepropanol

HRID 1600897Notes

Reaction equation

HRID 1600897 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:2]=1.[O:16]1[CH2:18][CH:17]1[CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.[H-].[Na+]>CN(C)C=O>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[CH:2]=[CH:1][C:6]([O:7][CH2:18][CH:17]([OH:16])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:5][CH:4]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 160694,4'-Dihydroxydiphenyl etherHCID 24758Sodium hydrideHCID 10877288HCID 10877288, compound

Product 1

HCID 21830679(+/-)-alpha-(4-(4-Hydroxyphenoxy)phenoxymethyl)-3-pyridinepropanolYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 5 from 4,4'-dihydroxydiphenyl ether (1.68 g), (±)-3-(2-oxiranylethyl)pyridine (1.24 g) and sodium hydride (60% dispersion in oil; 0.319 g) in dimethylformamide (20 ml) at 100° C. for 2 hours to give the title compound as a white solid (0.41 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cf4e03c9b79a465d8c6b4ca41e05df51
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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