Dimethylformamide → 3-Methyl-3-{[2-phenyl-3-(4-phenyl-3-butyl)-oxazolidin-5-yl]-methoxy}-pyridine

HRID 647976Notes

Reaction equation

HRID 647976 reaction equation
[C:1]1([CH:7]2[N:11]([CH:12]([CH3:21])[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17]C=3)[CH2:10][CH:9]([CH2:22][OH:23])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=1.[CH3:34]N(C)C=O>>[CH3:33][C:32]1([O:23][CH2:22][CH:9]2[O:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:11]([CH:12]([CH2:13][C:14]3[CH:15]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:21][CH3:34])[CH2:10]2)[CH:31]=[CH:30][CH:29]=[N:28][CH2:27]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2208322-Bromo-3-methylpyridineHCID 53876813[2-Phenyl-3-(4-phenylbutan-2-yl)-1,3-oxazolidin-5-yl]methanol

Product 1

HCID 705247363-Methyl-3-{[2-phenyl-3-(4-phenyl-3-butyl)-oxazolidin-5-yl]-methoxy}-pyridine

Procedure

31.1 g of 2-phenyl-3-(1-phenyl-3-butyl)-5-hydroxymethyl-oxazolidine, dissolved in 150 ml of dimethylformamide, are reacted with 6.5 g of sodium hydride dispersion (55% strength) and subsequently with 34.4 g of 2-bromo-3-methyl-pyridine over the course of 18 hours. Crude 3-methyl-3-{[2-phenyl-3-(4-phenyl-3-butyl)-oxazolidin-5-yl]-methoxy}-pyridine is thus obtained.

Sources & evidence

ORD record
ord-b9da533cac8b4745ad04c7951cc78c61
Source dataset
uspto-grants-1983_10
Patent number
US04410530

Reaction notes

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