Potassium Carbonate → HCID 13763324, compound

HRID 652506Notes

Reaction equation

HRID 652506 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].Br[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:23][O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][O:11][C:6]1[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79557Methyl 5-bromovalerateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13763324HCID 13763324, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.92 g of 1-(2,4-dihydroxy-3-propylphenyl) ethanone, 2.91 g of methyl 5-bromopentanoate and 3.1 g of anhydrous potassium carbonate in 35 ml of anhydrous dimethyl formamide was stirred and heated at 75° for 16 hours. The usual workup followed by chromatography on 350 g of silica gel and elution with 5% ethyl acetate-toluene gave 3.07 g (66% yield) of 5-(4-Acetyl-3-hydroxy-2-propylphenoxy) pentanoic acid methyl ester, the titled compound, as an oil.

Workup

  1. temperatureheated at 75° for 16 hours
  2. washThe usual workup followed by chromatography on 350 g of silica gel and elution with 5% ethyl acetate-toluene

Sources & evidence

ORD record
ord-c4da413ee9fd43a8b187c7b0ac3551f8
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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