Hydrochloric Acid → 6-(4-Ethoxycarbonylbutyl)oxycoumarin

HRID 611695Notes

Reaction equation

HRID 611695 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>CN(C)C=O>[CH2:23]([O:22][C:20]([CH2:19][CH2:18][CH2:17][CH2:16][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2)=[O:21])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 994776-hydroxy-2H-chromen-2-one

Product 1

HCID 150296966-(4-Ethoxycarbonylbutyl)oxycoumarin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

6-Hydroxycoumarin (405 mg; prepared in reference example 25) was dissolved in dry dimethylformamide (6 ml). Sodium hydride (60 mg) was added to the solution. The mixture was reacted for 15 min. Ethyl 5-bromopentanoate (0.48 ml) was added dropwise to the reaction solution. The mixture was stirred for 1 hr at 60° C. Ice-water was added to the reaction solution. The mixture was acidified with 1N hydrochloric acid. The mixture was extracted with ether. The extract was washed with water, dried anhydrous magnesium sulfate and then evaporated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1→2:1) to give the title compound (398 mg) having the following physical data.

Workup

  1. customThe mixture was reacted for 15 min
  2. extractionThe mixture was extracted with ether
  3. washThe extract was washed with water, dried anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-70f730533b69489a999e270ed3b71b83
Source dataset
uspto-grants-1999_12
Patent number
US06001877

Reaction notes

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