1,3-Dibromopropane → HCID 53811470, compound

HRID 342759Notes

Reaction equation

HRID 342759 reaction equation
[CH2:1]([C:3]1[C:4](=[O:17])[O:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([OH:13])[C:7]=2[CH2:14][CH2:15][CH3:16])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27]Br>CN(C=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>[Br:24][CH2:25][CH2:26][CH2:27][O:13][C:8]1[C:7]([CH2:14][CH2:15][CH3:16])=[C:6]2[C:11]([CH:12]=[C:3]([CH2:1][CH3:2])[C:4](=[O:17])[O:5]2)=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 53692562HCID 53692562, compound

Product 1

HCID 53811470HCID 53811470, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 3-ethyl-7-hydroxy-8-propylcoumarin (37 mg, 0.1593 mmol) and potassium carbonate (44 mg, 0.3186 mmol) in 0.7 mL DMF was added 1,3-dibromopropane (161 mg, 0.08 mL). The mixture was stirred at ambient temperature for 2 hours and diluted with ethyl acetate and saturated (aqueous) ammonium chloride. After the layers were separated, the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel (gradient elution: 5% then 10% then 20% ethyl acetate/hexane). This provided the title compound.

Workup

  1. customAfter the layers were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe crude residue was purified by flash chromatography on silica gel (
  8. washgradient elution

Sources & evidence

ORD record
ord-f014b9b8e69d466eac58dc6096419682
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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