Potassium Carbonate → 6-Hydroxymethyl-5-p-methoxybenzyloxy-2-methyl-4-pyrone

HRID 1461243Notes

Reaction equation

[OH:1][CH2:2][C:3]1[O:8][C:7]([CH3:9])=[CH:6][C:5](=[O:10])[C:4]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C)C=O>[OH:1][CH2:2][C:3]1[O:8][C:7]([CH3:9])=[CH:6][C:5](=[O:10])[C:4]=1[O:11][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 5.9 g of 6-hydroxymethyl-5-hydroxy-2-methyl-4-pyrone in 60 ml of dimethylformamide were successively added 6.2 g of potassium carbonate and 6.2 ml of p-methoxybenzyl chloride. The mixture was stirred at 70° C. for 2 hours. The reaction liquid was concentrated and 200 ml of water and 400 ml of dichloromethane were added to the concentrate. The organic phase was then washed with 200 ml of water. After drying over anhydrous magnesium sulfate, the organic phase was concentrated under reduced pressure. The concentrate was then separated and purified by flash column chromatography (eluting solution; chloroform: methanol=20:1) using Wako Gel C-300 (300 g) to give 5.9 g of the title compound.

Workup

customThe reaction liquid
concentrationwas concentrated
addition200 ml of water and 400 ml of dichloromethane were added to the concentrate
washThe organic phase was then 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 then separated
custompurified by flash column chromatography (eluting solution; chloroform: methanol=20:1)

Sources & evidence

ORD record: ord-81cbbc71b02f4cc5a62df3cd549f4e60
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075299

Reaction notes

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