Potassium Carbonate → HCID 67780727, compound

HRID 327960Notes

Reaction equation

HRID 327960 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][CH2:13][CH3:14].[CH3:15][O:16][C:17](=[O:33])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][O:16][C:17](=[O:33])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 152949972-[(5-Bromopentyl)oxy]benzenepropanoic acid methyl esterHCID 69824215HCID 69824215, compound

Product 1

HCID 67780727HCID 67780727, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.154 g (0.8 mmol) of 6-hydroxy-7-propyl-2H-benzofuran-3-one, 0.27 g (0.82 mmol) of 2-[(5-bromopentyl)oxy]benzenepropanoic acid methyl ester, 0.382 g (2.77 mmol) of anhydrous granular potassium carbonate, and 6 mL of anhydrous N,N-dimethylformamide was stirred at 60°-65° C. for 3 hr. The resulting slurry was cooled and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 7:3 and 6:4 hexane-ethyl acetate. There was obtained 0.24 g (68%) of 2-[5-[(2,3-dihydro-3-oxo-7-propylbenzofuran-6-yl)oxy]pentyloxy]benzenepropanoic acid methyl ester as a pale-yellow oil. A 0.1 g (0.227 mmol) sample of this material was dissolved in 10 mL of tetrahydrofuran and 1 mL of 3N aqueous HCl was added. The mixture was stirred at room temperature for 2.5 hr then heated at 60°-65° C. for 28 hr. After being stirred overnight at room temperature, the solution was diluted with water and worked-up with dichloromethane in the usual manner giving a viscous oil. Flash chromatography on silica gel, eluting with ethyl acetate and 9:1 ethyl acetate-methanol gave 0.04 g (41.5%) of 2-[ 5-[(2,3-dihydro-3-oxo-7-propylbenzofuran-6-yl)oxy]pentyloxy]benzenepropanoic acid as a pale-yellow gum which crystallized. Trituration of a sample with ether-hexane gave a pale-yellow solid, mp 101°-102.5° C.

Workup

  1. temperatureThe resulting slurry was cooled
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash chromatography on silica gel
  4. washeluting with 7:3 and 6:4 hexane-ethyl acetate

Sources & evidence

ORD record
ord-e58ec23888224829b4415d1a5a564f42
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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