Sodium Hydroxide → HCID 22010353, compound

HRID 322894Notes

Reaction equation

HRID 322894 reaction equation
[C:1]([C:4]([C:6]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[CH:24][C:7]=1[O:8][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[O:5])([OH:3])=[O:2].[OH-].[Na+]>O1CCOCC1>[C:1]([C:4]([C:6]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[CH:24][C:7]=1[O:8][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:5])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54430731HCID 54430731, compound

Product 1

HCID 22010353HCID 22010353, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of ethyl (RS)-4-(2-carboxycarbonyl-5-(3-thienylmethoxy)phenoxy)-4-(2-methylphenyl)butanoate (0.37 g) and 1 N sodium hydroxide (2.7 mL) in dioxan (6.6 mL) is heated at 60° C. for 1.5 hours. The reaction mixture is evaporated and the residue dissolved in water (5 mL). The pH of the solution is adjusted to 1 by addition of 1 N hydrochloric acid and the mixture extracted with ethyl acetate (20 mL). The organic phase is dried over magnesium sulphate and evaporated. The residual yellow oil is triturated with ether to give (RS)-4-(2-Carboxycarbonyl-5-(3-thienylmethoxy)phenoxy)-4-(2-methylphenyl)butanoic acid as a yellow solid (0.29 g), m.p. 173-175° C. [Elemental analysis:- C,63.2; H,5.07%. Calculated:- C,63.4; H,4.88%].

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue dissolved in water (5 mL)
  3. additionThe pH of the solution is adjusted to 1 by addition of 1 N hydrochloric acid
  4. extractionthe mixture extracted with ethyl acetate (20 mL)
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customevaporated
  7. customThe residual yellow oil is triturated with ether

Sources & evidence

ORD record
ord-0e23a8182da7481db4676d2021657941
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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