Sodium Hydroxide → (RS)-5-(3-benzylthiophenyl)-4-(2-methylphenyl)-5-oxopentanoic acid hemihydrate

HRID 322892Notes

Reaction equation

HRID 322892 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([C:15](=[O:31])[CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[OH2:20].[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([C:15](=[O:31])[CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([C:15](=[O:31])[CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54196646HCID 54196646, compound

Product 1

HCID 131722482(RS)-5-(3-benzylthiophenyl)-4-(2-methylphenyl)-5-oxopentanoic acid hemihydrateYield 103.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of ethyl (RS)-5-(3-benzylthiophenyl)-4-(2-methylphenyl)-5-oxopentanoate (0.56 g) and 1 N sodium hydroxide (3.4 mL) in dioxan (11 mL) is heated at 70° C. for 1.5 hours. The reaction mixture is evaporated and the residue dissolved in water (6 mL). The pH of the solution is adjusted to pH 1 by addition of 2 N hydrochloric acid and the mixture extracted with ether (20 mL). The organic phase is washed twice with water (6 mL), dried over magnesium sulphate and evaporated. The residual orange oil (0.59 g) is triturated with pentane and crystallised from cyclohexane to give (RS)-5-(3-benzylthiophenyl)-4-(2-methylphenyl)-5-oxopentanoic acid hemihydrate as a pale yellow solid (0.37 g), m.p.105-107° C. [Elemental analysis:- C,72.4; H,5.94%. Calculated for C25H24O3S.0.5H2O:- C,72.4; H,5.91%].

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue dissolved in water (6 mL)
  3. additionThe pH of the solution is adjusted to pH 1 by addition of 2 N hydrochloric acid
  4. extractionthe mixture extracted with ether (20 mL)
  5. washThe organic phase is washed twice with water (6 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residual orange oil (0.59 g) is triturated with pentane
  9. customcrystallised from cyclohexane

Sources & evidence

ORD record
ord-39c6beb38f4c4f95b1fd4d32cd8f8474
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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