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

HRID 1246414Notes

Reaction equation

HRID 1246414 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-d9dcb3a7ded148fbb0d6f7b34561032e
Source dataset
uspto-grants-2006_10
Patent number
US07126012B2

Reaction notes

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