Potassium Carbonate → HCID 53873785, compound

HRID 328046Notes

Reaction equation

HRID 328046 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:12]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br)[CH:11]=[CH:10][C:9]=2[N:8]=1)[CH3:2].[OH:32][C:33]1[CH:43]=[CH:42][C:36]2[C:37](=[O:41])[CH2:38][CH2:39][O:40][C:35]=2[C:34]=1[CH2:44][CH2:45][CH3:46].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:12]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:32][C:33]3[CH:43]=[CH:42][C:36]4[C:37](=[O:41])[CH2:38][CH2:39][O:40][C:35]=4[C:34]=3[CH2:44][CH2:45][CH3:46])[CH:11]=[CH:10][C:9]=2[N:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one2×HCID 54274067HCID 54274067, compound

Product 1

HCID 53873785HCID 53873785, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.96 g of the partially purified 6-[(5-bromopentyl)oxy]-2,5-quinolinedipropanoic acid diethyl ester from the preceding example, 0.402 g (1.95 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, 1.08 g (7.8 mmol) of anhydrous granular potassium carbonate and 25 mL of 2-butanone was stirred at 90° C. for 18 hr. A second portion of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one (0.117 g, 0.57 mmol) was added and the reaction was continued for another 22.5 hr. The mixture was cooled and filtered through anhydrous magnesium sulfate and the solids were washed with ethyl acetate. The filtrate and washes were combined and concentrated under reduced pressure. The crude product was purified by flash chromatography on 110 g of silica gel, eluting with hexane-ethyl acetate (5:2) to give 0.66 g (54.8%) of the title compound as a white solid, mp 59°-61° C.

Workup

  1. waitthe reaction was continued for another 22.5 hr
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through anhydrous magnesium sulfate
  4. washthe solids were washed with ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on 110 g of silica gel
  7. washeluting with hexane-ethyl acetate (5:2)

Sources & evidence

ORD record
ord-27cbd2549326486980014b98e1885ddc
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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