Triethylsilane → Ethyl 4-([1,1'-biphenyl]-4-yl)butanoate

HRID 2352572Notes

Reaction equation

HRID 2352572 reaction equation
C([SiH](CC)CC)C.[C:8]1([C:14]2[CH:28]=[CH:27][C:17]([C:18]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=O)=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>FC(F)(F)C(O)=O.O>[C:8]1([C:14]2[CH:28]=[CH:27][C:17]([CH2:18][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 12600094Ethyl 4-oxo-4-(4-phenylphenyl)butanoate

Product 1

HCID 19843451Ethyl 4-([1,1'-biphenyl]-4-yl)butanoateYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (32.62 ml) was added in one portion to a stirred solution of ethyl 3-(4-phenylbenzoyl)propanoate [(2), 25.06 g] in trifluoroacetic acid (71.5 ml) and the resulting mixture was stirred at room temperature for about 20 hours. The resulting clear dark orange solution was diluted with water and extracted with ether. The extracts were washed with aqueous sodium bicarbonate (x2) and then water (x2), dried and concentrated to give a mobile brown liquid. Triethylsilane remaining in this liquid was removed by Kugelrohr evaporative distillation at 110° C. and a pressure of ca. 1 mmHg to leave crude ethyl 4-(4-phenylphenyl)butanoate (21.20 g) as a brown oil. (Compare method of C. T. West, S. J. Donnelly, D. A. Kooistra and M. P. Doyle, J. Org. Chem., 1973, 38, 2675).

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with aqueous sodium bicarbonate (x2)
  3. dry with materialwater (x2), dried
  4. concentrationconcentrated
  5. customto give a mobile brown liquid
  6. customTriethylsilane remaining in this liquid was removed by Kugelrohr evaporative distillation at 110° C.

Sources & evidence

ORD record
ord-9ee1429c92e7409bbc4d2a2d32de4ee8
Source dataset
uspto-grants-1989_10
Patent number
US04877811

Reaction notes

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