Potassium Carbonate → HCID 53993889, compound

HRID 1648008Notes

Reaction equation

HRID 1648008 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:10][CH:9]=[CH:8][C:7]=1[OH:19].Br[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:10][CH:9]=[CH:8][C:7]=1[O:19][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 53947583HCID 53947583, compound

Product 1

HCID 53993889HCID 53993889, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the 2-hydroxy-6-[(5-hydroxypentyl)oxy]benzenepropanoic acid methyl ester from the preceding example (1.4 g; 4.96 mmol), 1.13 g (5.4 mmol) of ethyl 5-bromovalerate, 1.57 g (11.4 mmol) of anhydrous, granular potassium carbonate, and 12 mL of dimethyl sulfoxide was stirred at room temperature for 6 hr. The resulting slurry was filtered with suction and the solids were washed well with ethyl acetate. The filtrate and washed were combined and treated with water. Work-up with ether in the usual manner gave an oily product which was purified by chromatography on silica gel. Elution with 1:3 hexane-ether afforded 1.0 g (49.3%) of 6-[(5-hydroxypentyl)oxy]-2-(5-ethoxy-5-oxopentyloxy)benzenepropanoic acid methyl ester as an oil.

Workup

  1. filtrationThe resulting slurry was filtered with suction
  2. washthe solids were washed well with ethyl acetate
  3. washThe filtrate and washed
  4. additiontreated with water
  5. customgave an oily product which
  6. customwas purified by chromatography on silica gel
  7. washElution with 1:3 hexane-ether

Sources & evidence

ORD record
ord-ac3f67badeca462fb0af3883835afd83
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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