Potassium Carbonate → HCID 19980208, compound

HRID 1461247Notes

Reaction equation

HRID 1461247 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[O:13][C:12]([CH2:14][OH:15])=[CH:11][C:10](=[O:16])[C:9]=2[OH:17])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1>CN(C)C=O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[O:13][C:12]([CH2:14][OH:15])=[CH:11][C:10](=[O:16])[C:9]=2[O:17][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 2616163-hydroxy-6-(hydroxymethyl)-2-(morpholinomethyl)-4H-pyran-4-one

Product 1

HCID 19980208HCID 19980208, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 5.45 g of 6-morpholinomethyl-5-hydroxy-2-hydroxymethyl-4-pyrone in 50 ml of dimethylformamide were successively added 3.32 g of potassium carbonate and 4 ml of p-methoxybenzyl chloride. The mixture was stirred at 70° C. for 4 hours and at room temperature for a further 17 hours. The reaction liquid was concentrated and 100 ml of water and 200 ml of dichloromethane were added to the concentrate. The organic phase was then washed with 100 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 (200 g) to give 1.8 g of the title compound.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. addition100 ml of water and 200 ml of dichloromethane were added to the concentrate
  4. washThe organic phase was then washed with 100 ml of water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. concentrationthe organic phase was concentrated under reduced pressure
  7. customThe concentrate was then separated
  8. custompurified by flash column chromatography (eluting solution; chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-204ba0235d324c73a1d849bcee46a5dd
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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