Triethylsilane → 4-(4-Ethylphenyl)butanoic acid

HRID 2887

Reaction equation

HRID 2887 reaction equation
C([SiH](CC)CC)C.O=[C:9]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[CH2:10][CH2:11][C:12]([OH:14])=[O:13]>FC(F)(F)C(O)=O>[CH2:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)[CH3:22]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 3169834-(4-Ethylphenyl)-4-oxobutanoic acid

Product 1

HCID 2316064-(4-Ethylphenyl)butanoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In a 100-cm3 flask, 2.5 g of 4-oxo-4-(4-ethylphenyl)butyric acid are dissolved with magnetic stirring in 19 cm3 of trifluoroacetic acid. 3.2 g of triethylsilane are added dropwise. The reaction mixture is stirred for 86 hours at room temperature. It is poured into ice. It is extracted with 3 volumes of ether. The organic phases are washed 3 times with 10% potassium carbonate solution. The aqueous phases are combined and then acidified by adding concentrated hydrochloric acid until the pH is 3-4. The precipitate obtained is drained and then recrystallized.

Workup

  1. additionIt is poured into ice
  2. extractionIt is extracted with 3 volumes of ether
  3. washThe organic phases are washed 3 times with 10% potassium carbonate solution
  4. additionby adding concentrated hydrochloric acid until the pH is 3-4
  5. customThe precipitate obtained
  6. customrecrystallized

Sources & evidence

ORD record
ord-ff41cf49840a4862bb629df3394008db
Source dataset
uspto-grants-1998_03
Patent number
US05731352

Linked notes

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