Potassium Carbonate → HCID 12513693, compound

HRID 495147Notes

Reaction equation

HRID 495147 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.Br[CH2:14][CH2:15][CH:16]=[CH2:17].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:17]([O:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][C:4](=[O:12])[CH:3]=1)[CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 546829304-Hydroxycoumarin

Product 1

HCID 12513693HCID 12513693, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

4-Hydroxycoumarin (10.93 mmol, 1.77 g), 4-bromo-1-butene (10.93 mmol, 1.48 g) and K2CO3 (33 mmol, 4.55 g) is suspended in 50 mL of acetone, and the reaction is heated to 55° C. for 2.5 days the reaction mixture is filtered and the filtrate is evaporated under reduced pressure. A small amount of the resulting solid is purified by column chromatography to afford an analytically pure sample of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 7.78 (1H, dd, J=1.5, 7.75 Hz), 7.66 (1H, m), 7.38 (2H, m), 5.93 (1H, m), 5.92 (1H, s), 5.20 (2H, m), 2.59 (2H, m), 2.50 (2H, m); MS (ESI, Pos.) calcd for C13H12O3 m/z [M+H]=217.1, found 217.1.

Workup

  1. filtrationis filtered
  2. customthe filtrate is evaporated under reduced pressure
  3. customA small amount of the resulting solid is purified by column chromatography

Sources & evidence

ORD record
ord-95fbce5561c3495e9a23b120a260cb47
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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