Potassium Carbonate → 2-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromone

HRID 1285243Notes

Reaction equation

HRID 1285243 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[C:10]([OH:17])[C:9]=1[CH2:18][CH2:19][CH3:20].[C:21]([C:26]1[O:27][C:28]2[C:33]([C:34](=[O:36])[CH:35]=1)=[CH:32][CH:31]=[C:30]([OH:37])[C:29]=2[CH2:38][CH2:39][CH3:40])([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Ca+2].[Cl-]>CN(C)C=O>[C:21]([C:26]1[O:27][C:28]2[C:33]([C:34](=[O:36])[CH:35]=1)=[CH:32][CH:31]=[C:30]([O:37][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[C:10]([OH:17])[C:9]=1[CH2:18][CH2:19][CH3:20])[C:29]=2[CH2:38][CH2:39][CH3:40])([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 4196515Ethyl 7-hydroxy-4-oxo-8-propyl-4H-chromene-2-carboxylateHCID 5284359Calcium ChlorideHCID 137632981-Bromo-5-[2-n-propyl-3-hydroxy-4-acetylphenoxy]-pentane

Product 1

HCID 135378612-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromoneYield 44.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.67 g (13.6 mmole) of 1-bromo-5-[2-n-propyl-3-hydroxy-4-acetylphenoxy]-pentane, 2.39 g (8.65 mmole) of 2-carboethoxy-7-hydroxy-8-n-propylchromone, and 2.76 g (20 mmole) of anhydrous potassium carbonate were dissolved in 100 ml dimethylformamide in a 250 ml single neck round bottom flask equipped with a magnetic stirring bar and a drying tube charged with calcium chloride. The contents of the flask were stirred at 70° for 18 hours. After cooling, the reaction solution was filtered and the dimethylformamide removed by rotary evaporation. The residual dark red oil was dissolved in 50% ethyl acetate/hexane and purified by chromatography to give 2.07 g (44%) of the title compound, mp 90°-91°. Calc: C, 69.13; H, 7.11; Found: C, 69.44; H, 7.44.

Workup

  1. customequipped with a magnetic stirring bar and a drying tube
  2. temperatureAfter cooling
  3. filtrationthe reaction solution was filtered
  4. customthe dimethylformamide removed by rotary evaporation
  5. dissolutionThe residual dark red oil was dissolved in 50% ethyl acetate/hexane
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-22ba96479d904a9daed5b1d8e72c43c7
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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