Hydrochloric Acid → HCID 15595182, compound

HRID 1906212Notes

Reaction equation

HRID 1906212 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:24]=[CH:23][C:9]2[C:10](=[O:22])[CH2:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]I)([CH3:14])[O:13][C:8]=2[C:7]=1[CH2:25][CH2:26][CH3:27].[CH3:29][CH2:30][CH2:31][C:32]1[C:37]([OH:38])=[C:36]([C:39]([CH3:41])=[O:40])[CH:35]=[CH:34][C:33]=1[OH:42].C(=O)(O)[O-].[K+].Cl>CN(C)C=O.CC(C)=O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:24]=[CH:23][C:9]2[C:10](=[O:22])[CH2:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:42][C:33]3[CH:34]=[CH:35][C:36]([C:39](=[O:40])[CH3:41])=[C:37]([OH:38])[C:32]=3[CH2:31][CH2:30][CH3:29])([CH3:14])[O:13][C:8]=2[C:7]=1[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516893Potassium BicarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 15595181HCID 15595181, compound

Product 1

HCID 15595182HCID 15595182, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.25 g of the iodohexyl chromanone product from Example 4, 0.49 g of 2,4-dihydroxy-3-propylacetophenone, 0.841 g of anhydrous potassium bicarbonate, 25 ml of acetone, and 12 ml of N,N-dimethylformamide was refluxed and stirred for 6 hours. The resulting mixtures was cooled, poured into cold 1N hydrochloric acid, and extracted 3 times with ether. The combined ether extracts were washed with saturated aqueous sodium bicarbonate, water, and brine, then dried (magnesium sulfate), filtered and concentrated in vacuo giving 1.5 of an oil. This material was chromatographed on 45 g of silica gel. Elution with 2:1 hexane-ethyl acetate afforded 1.18 g (83.4%) of rac-[[2-[6-(4-acetyl-3-hydroxy-2-propylphenoxy)-hexyl]-3,4-dihydro-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid methyl ester as a colorless oil.

Workup

  1. temperaturewas refluxed
  2. temperatureThe resulting mixtures was cooled
  3. extractionextracted 3 times with ether
  4. washThe combined ether extracts were washed with saturated aqueous sodium bicarbonate, water, and brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customgiving 1.5 of an oil
  9. customThis material was chromatographed on 45 g of silica gel
  10. washElution with 2:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-957239d1c1924be18ddb900cc6af30ad
Source dataset
uspto-grants-1987_03
Patent number
US04650812

Reaction notes

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