Acetone → HCID 14329882, compound

HRID 2231917Notes

Reaction equation

HRID 2231917 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)=[CH:15][C:8]=2[O:7]1)=[O:5])[CH3:2].[OH:23][C:24]1[C:29]([CH2:30][CH2:31][CH3:32])=[C:28]([OH:33])[CH:27]=[CH:26][C:25]=1[C:34](=[O:36])[CH3:35].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CCOCC.CN(C)C=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:33][C:28]3[CH:27]=[CH:26][C:25]([C:34](=[O:36])[CH3:35])=[C:24]([OH:23])[C:29]=3[CH2:30][CH2:31][CH3:32])=[CH:15][C:8]=2[O:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 53737436HCID 53737436, compound

Product 1

HCID 14329882HCID 14329882, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.2 g (3.23 mmoles) of racemic-7-[(5-bromopentyl)oxy]-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid ethyl ester, 1.0 g (5.15 mmoles) of 2',4'-dihydroxy-3'-propylacetophenone, 1.8 g (13.0 mmoles) of anhydrous potassium carbonate, 30 ml of acetone, and 15 ml of N,N-dimethylformamide was stirred and refluxed for 6 hr. After being cooled, the mixture was diluted with ether. The ether phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (2.1 g) was chromatographed on 50 g of silica gel. Elution with 19:1 toluene-ethyl acetate afforded 1.3 g (83%) of racemic-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid ethyl ester as a yellow oil.

Workup

  1. temperaturerefluxed for 6 hr
  2. temperatureAfter being cooled
  3. washThe ether phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue (2.1 g) was chromatographed on 50 g of silica gel
  8. washElution with 19:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-73c7193dd256487aaf45d2e49edb8574
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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