Potassium Carbonate → HCID 19980215, compound

HRID 1461234Notes

Reaction equation

[CH3:1][C:2]1[O:7][C:6](O)=[CH:5][C:4](=[O:9])[C:3]=1[OH:10].[C:11](=O)([O-])[O-:12].[K+].[K+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C)C=O>[CH3:1][C:2]1[O:7][C:6]([CH2:11][OH:12])=[CH:5][C:4](=[O:9])[C:3]=1[O:10][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 5 g of 6-methyl-5-hydroxy-2-hydroxy-4-pyrone in 60 ml of dimethylformamide were successively added 6.8 g of potassium carbonate and 6.2 g of p-methoxybenzyl chloride. The mixture was stirred at 60° C. for 6 hours. After the reaction mixture was concentrated, 200 ml of water and 400 ml of dichloromethane were added to the concentrate. The organic phase was washed with 200 ml of water. After drying over anhydrous magnesium sulfate, the organic phase was concentrated under reduced pressure. The concentrate was separated and purified by flash column chromatography (eluting solution; chloroform: methanol=20:1) using Wako Gel C-300 (manufactured by Wako Pure Chemical Industry Co., Ltd.) (100 g) to give 5.3 g of the title compound.

Workup

concentrationAfter the reaction mixture was concentrated
addition200 ml of water and 400 ml of dichloromethane were added to the concentrate
washThe organic phase was washed with 200 ml of water
dry with materialAfter drying over anhydrous magnesium sulfate
concentrationthe organic phase was concentrated under reduced pressure
customThe concentrate was separated
custompurified by flash column chromatography (eluting solution; chloroform: methanol=20:1)

Sources & evidence

ORD record: ord-c55e8ab1683d471ba6aa5395daa41d5a
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075299

Reaction notes

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