4-[4-(methylthio)phenyl]-4-oxobutanoic acid → 116174-33-5

HRID 985775Notes

Reaction equation

HRID 985775 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.[H-].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 20637154-[4-(methylthio)phenyl]-4-oxobutanoic acidHCID 131724811HCID 131724811, compound

Product 1

HCID 21916663116174-33-5

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 ml round-bottomed flask, 0.088 mol of the compound obtained in Step A is dissolved in 0.881 ml of trifluoroacetic acid. The solution is cooled to 0° C. with the aid of an ice bath and 0.220 ml of triethylsilane hydride is added with the aid of a dropping funnel. The reaction mixture is stirred for 18 hours at ambient temperature and is then hydrolysed. The precipitate formed is filtered off under suction, is washed with water and with cyclohexane and is then dissolved in ethyl acetate. The organic phase is dried over MgSO4 and evaporated to obtain the title product in the form of a white solid.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off under suction
  3. washis washed with water and with cyclohexane
  4. dissolutionis then dissolved in ethyl acetate
  5. dry with materialThe organic phase is dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-be3d8eb2fae044a7ade46c3559bcb064
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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