Potassium Carbonate → HCID 53730862, compound

HRID 328033Notes

Reaction equation

HRID 328033 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)=[C:11]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=1)[CH3:2].[OH:30][C:31]1[CH:41]=[CH:40][C:34]2[C:35](=[O:39])[CH2:36][CH2:37][O:38][C:33]=2[C:32]=1[CH2:42][CH2:43][CH3:44].C(=O)([O-])[O-:46].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][C:8](=[O:46])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:30][C:31]2[CH:41]=[CH:40][C:34]3[C:35](=[O:39])[CH2:36][CH2:37][O:38][C:33]=3[C:32]=2[CH2:42][CH2:43][CH3:44])=[C:11]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 54369773HCID 54369773, compound

Product 1

HCID 53730862HCID 53730862, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1.69 g (3.58 mmol) of 4-(5-bromopentyloxy)-3-(3-ethoxy-3-oxopropyl)benzenepentanoic acid ethyl ester from the preceding example, 0.738 g (3.58 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, 2.07 g (14.98 mmol) of anhydrous potassium carbonate, and 37.5 mL of 2-butanone was stirred and refluxed for 18.5 hr. After being cooled to room temperature, the mixture was filtered through anhydrous magnesium sulfate and the solids were washed thoroughly with ethyl acetate. The filtrate and washes were combined and concentrated in vacuo and the crude product was purified by flash chromatography on 250 g of silica gel, eluting with hexane-ethyl acetate (4:1). There was obtained 1.93 g (90.1%) of the title compound as a colorless oil.

Workup

  1. temperaturerefluxed for 18.5 hr
  2. filtrationthe mixture was filtered through anhydrous magnesium sulfate
  3. washthe solids were washed thoroughly with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customthe crude product was purified by flash chromatography on 250 g of silica gel
  6. washeluting with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-53d85a8b0180479e9519e244db138a08
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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