Potassium Carbonate → HCID 53855288, compound

HRID 327980Notes

Reaction equation

HRID 327980 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]2[C:12](=[O:16])[CH2:13][CH2:14][O:15][C:10]=2[C:9]=1[CH2:19][CH2:20][CH3:21].[CH2:22]([O:24][C:25](=[O:46])[CH2:26][CH2:27][C:28]1[CH:33]=[C:32]([C:34]2[O:35][C:36](=[O:44])[C:37]3[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=3[CH:39]=2)[CH:31]=[CH:30][C:29]=1[OH:45])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:22]([O:24][C:25](=[O:46])[CH2:26][CH2:27][C:28]1[CH:33]=[C:32]([C:34]2[O:35][C:36](=[O:44])[C:37]3[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=3[CH:39]=2)[CH:31]=[CH:30][C:29]=1[O:45][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]2[C:12](=[O:16])[CH2:13][CH2:14][O:15][C:10]=2[C:9]=1[CH2:19][CH2:20][CH3:21])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19921918HCID 19921918, compoundHCID 54115240HCID 54115240, compound

Product 1

HCID 53855288HCID 53855288, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 0.352 g (0.99 mmol) of 7-[(5-bromopentyl)oxy]-2,3-dihydro-8-propyl-4H-1-benzopyran-4-one, 0.346 g (1.02 mmol) of 2-hydroxy-5-(1-oxo-1H-2-benzopyran-3-yl)benzenepropanoic acid ethyl ester, 0.574 g (4.15 mmol) of anhydrous granular potassium carbonate and 20.9 mL of 2-butanone was stirred and refluxed for 45 hrs. The resulting slurry was filtered with suction and the solids were 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, affording 0.352 g (58.1%) of the title compound as a white solid, mp 143.5°-144° C.

Workup

  1. temperaturerefluxed for 45 hrs
  2. filtrationThe resulting slurry was filtered with suction
  3. washthe solids were 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-570036ffa3554c929cf2de5f9f7239ce
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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