HCID 86756592, compound → HCID 22010338, compound

HRID 322909Notes

Reaction equation

HRID 322909 reaction equation
[O:1]=[C:2]([CH2:8][C:9](=[O:33])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)=[CH:12][C:11]=1[O:23][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])[CH3:25])[C:3]([O:5]CC)=[O:4]>[OH-].[K+]>[O:1]=[C:2]([CH2:8][C:9](=[O:33])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)=[CH:12][C:11]=1[O:23][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])[CH3:25])[C:3]([OH:5])=[O:4]

Participants

3

Reactant 1

HCID 86756592HCID 86756592, compound

Product 1

HCID 22010338HCID 22010338, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of ethyl (RS)-2,4-dioxo-4-[2-(1-(2-methylphenyl)ethoxy)-4-(3-thienylmethoxy)phenyl]butanoate (0.38 g) in 15% methanolic potassium hydroxide (25 mL) is stirred at reflux for 1 hour before being cooled and concentrated under reduced pressure. The residue is dissolved in water, acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer is dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is recrystallised from cyclohexane to give (RS)-2,4-dioxo-4-[2-(1-(2-methylphenyl)ethoxy)-4-(3-thienylmethoxy)-phenyl]butanoic acid (35 mg) as a yellow solid, m.p. 124-6° C. [Elemental analysis:- C, 65.82; H, 5.03%; Calculated for C24H22O6S:- C, 65.74; H, 5.06%].

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturebefore being cooled
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue is dissolved in water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is recrystallised from cyclohexane

Sources & evidence

ORD record
ord-f6216ebce60743b097dec4fe5b0333fa
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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