Water → 6-Hydroxymethyl-3-(p-methoxybenzyl)oxy-1-(p-methoxybenzyl)-4-pyridone

HRID 704649Notes

Reaction equation

HRID 704649 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[CH:7][CH:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:5](=[O:19])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1.O>CN(C)C=O.ClCCl>[OH:1][CH2:2][C:3]1[N:8]([CH2:32][C:31]2[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)[CH:7]=[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:5](=[O:19])[CH:4]=1.[OH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:5]([O:19][CH2:32][C:31]2[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)[CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 200727056-Hydroxymethyl-3-(p-methoxybenzyl)oxy-4-pyridone

Product 2

HCID 151595336-Hydroxymethyl-3-(p-methoxybenzyl)oxy-1-(p-methoxybenzyl)-4-pyridoneHCID 156625066-Hydroxymethyl-3,4-bis[(p-methoxybenzyl)oxy]-pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2.613 g of 6-hydroxymethyl-3-(p-methoxybenzyl)oxy-4-pyridone in 100 ml of dimethyl-formamide were added sequentially 2.073 g of potassium carbonate and 2.35 g of p-methoxybenzyl chloride, and the mixture is stirred at room temperature for 40 hours. The reaction mixture is added to 200 ml of water and 400 ml of dichloromethane, and the organic layer is washed with 200 ml of water. The organic layer is dried over anhydrous magnesium sulfate, condensed under reduced pressure and subjected to flash column chromatography on 100 g of Wako-Gel C-300 (manufactured by Wako Pure Chemical Industries, Ltd.) with an eluent of chloroformmethanol (20:1) to perform separation and purification. 6-hydroxymethyl-3-(p-methoxybenzyl)oxy-1-(p-methoxybenzyl)-4-pyridone and 6-hydroxymethyl-3,4-bis[(p-methoxybenzyl)oxy]-pyridine are obtained as colorless crystals in amounts of 1.749 g and 1.527 g, respectively. 6-hydroxymethyl-3-(p-methoxybenzyl)oxy-1-(p-methoxybenzyl)-4-pyridone;

Workup

  1. washthe organic layer is washed with 200 ml of water
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulfate, condensed under reduced pressure
  3. customseparation and purification

Sources & evidence

ORD record
ord-3df84765f60440cd8804a64923c80778
Source dataset
uspto-grants-1991_01
Patent number
US04988686

Reaction notes

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