Hydrochloric Acid → HCID 21758989, compound

HRID 2211397Notes

Reaction equation

HRID 2211397 reaction equation
[CH2:1]([C:3]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:22]([O:32]C(=O)C)=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH2:1]([C:3]1[CH:24]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:22]([OH:32])=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 67626985HCID 67626985, compound

Product 1

HCID 21758989HCID 21758989, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2-(3-(2-Ethyl-4-(4-fluorophenyl)-5-acetoxyphenoxy)propoxy)phenyl)-E-propenoic acid (90 mg, 0.2 mmol) was dissolved in methanol (10 mL). 0.1M Aqueous potassium carbonate solution was added and the solution stirred under nitrogen overnight. The thin-layer chromatogram showed a single spot of the same Rf as the starting material so additional 1.0M potassium carbonate solution was added and the solution stirred for a further 4 hours. The reaction mixture was poured into 1M hydrochloric acid (50 mL) and the mixture extracted 3 times with chloroform. The combined chloroform extracts were dried with magnesium sulfate and evaporated to provide 63 mg of the title intermediate as an oil which solidified to a glass. MS, NMR.

Workup

  1. additionwas added
  2. stirringthe solution stirred for a further 4 hours
  3. extractionthe mixture extracted 3 times with chloroform
  4. dry with materialThe combined chloroform extracts were dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d4a699f351dc446795eac897717c322d
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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