Potassium Carbonate → HCID 54137440, compound

HRID 327997Notes

Reaction equation

HRID 327997 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[O:7]2.Br[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[C:3]2[CH:4]=[CH:5][C:6](=[O:12])[O:7][C:8]=2[CH:9]=[CH:10][CH:11]=1)[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 53181792H-1-Benzopyran-2-one, 5-hydroxy-

Product 1

HCID 54137440HCID 54137440, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2.25 g (18.6 mmol) of 5-hydroxycoumarin, 4.2 g (20 mmol) of ethyl 5-bromovalerate, 7.0 g (50 mmol) of anhydrous, granular potassium carbonate, and 10 mL of dimethyl sulfoxide was stirred at room temperature for 24 hr. The resulting slurry was filtered with suction and the solids washed well with ethyl acetate. The filtrate and washes were combined and poured into water and the mixture was worked-up with ethyl acetate in the usual manner. The semi-solid residue was triturated and washed with hexane giving 2.36 g (44%) of 5-[(2-oxo-2H-1-benzopyran-5-yl)oxy]pentanoic acid ethyl ester as a tan solid.

Workup

  1. filtrationThe resulting slurry was filtered with suction
  2. washthe solids washed well with ethyl acetate
  3. additionpoured into water
  4. customThe semi-solid residue was triturated
  5. washwashed with hexane giving 2.36 g (44%) of 5-[(2-oxo-2H-1-benzopyran-5-yl)oxy]pentanoic acid ethyl ester as a tan solid

Sources & evidence

ORD record
ord-9305be2b43fd44ff905d859107505550
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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