Potassium Carbonate → HCID 53691388, compound

HRID 327947Notes

Reaction equation

HRID 327947 reaction equation
O[C:2]1C=CC2C(=O)[CH2:7][CH2:8][O:9][C:4]=2[C:3]=1CCC.C(OC(=O)CC[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:31]=1)=[O:29])C.C(=O)([O-])[O-:43].[K+].[K+]>CC(=O)CC>[CH2:8]([O:9][C:4](=[O:43])[CH2:3][CH2:2][C:27]1[CH:22]=[C:23]([C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:31]=2)=[O:29])[CH:24]=[CH:25][CH:26]=1)[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 131718297HCID 131718297, compound

Product 1

HCID 53691388HCID 53691388, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 0.144 g (0.70 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, 0.371 g (0.70 mmol) of 2-[(6-bromohexyl)oxy]-5[[(3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester, 0.479 g (3.47 mmol) of anhydrous granular potassium carbonate and 13.1 mL of 2-butanone was stirred and refluxed for 18 hr. The resulting slurry was filtered with suction and the solids washed thoroughly with ethyl acetate. The filtrate and washes were combined and concentrated in vacuo and the residue was purified by flash chromatography on 75 g of silica gel, eluting with 3:1 hexane-ethyl acetate, giving 0.37 g (80.6%) of 2-[6-[2,3-dihydro-4-oxo-8-propyl-4H-1-benzopyran-7-yl)oxy]hexyloxy]-5-[[3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester as a white solid, mp 58°-59.5° C. A mixture of 0.331 g (0.50 mmol) of this ester in 6 mL of THF and 6 mL of water was treated with 64.7 mg (1.54 mmol) of lithium hydroxide monohydrate and the resulting mixture was stirred for 25.5 hr at room temperature, before being acidified with 17 mL of 3N aqueous sulfuric acid. Work-up with ethyl acetate in the usual manner gave a crude product which was recrystallized from hexane-ethyl acetate affording 0.242 g (79.7%) of the title compound as a white solid, mp 169°-172° C.

Workup

  1. temperaturerefluxed for 18 hr
  2. filtrationThe resulting slurry was filtered with suction
  3. washthe solids washed thoroughly with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash chromatography on 75 g of silica gel
  6. washeluting with 3:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-a8cdbd236dbc44f79820afceb398bd14
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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