Potassium Carbonate → 3-(3-Oxo-butoxy)-chromen-2-one

HRID 592126

Reaction equation

HRID 592126 reaction equation
[OH:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Cl[CH2:38][CH2:39][C:40](=[O:42])[CH3:41]>C1COCC1>[O:42]=[C:40]([CH3:41])[CH2:39][CH2:38][O:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 136503-HydroxycoumarinHCID 2855718-Crown-6HCID 806084-Chloro-2-butanone

Product 1

HCID 867104563-(3-Oxo-butoxy)-chromen-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-chromen-2-one (16.2 g, 100 mmol) is dissolved into 100 mL of anhydrous THF in a three neck flask equipped with a condenser, stir bar, and argon inlet. To the mixture is added 27.6 g (200 mmol) of anhydrous potassium carbonate and 2.0 g of 18-crown-6. 4-Chloro-2-butanone (15.9 g, 150 mmol) is added and the system is refluxed for 16 hours, cooled to room temperature, filtered, and the organic solvents are removed by rotary evaporation. The solid organic residue is purified by column chromatography using 3:1 ethyl acetate:hexanes to yield 3-(3-oxo-butoxy)-chromen-2-one.

Workup

  1. customequipped with a condenser
  2. temperaturethe system is refluxed for 16 hours
  3. filtrationfiltered
  4. customthe organic solvents are removed by rotary evaporation
  5. customThe solid organic residue is purified by column chromatography

Sources & evidence

ORD record
ord-c7c5525a42064e41aa5025e479a30888
Source dataset
uspto-grants-2016_01
Patent number
US09238712B2

Linked notes

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