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

HRID 2352572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2352572
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-9ee1429c92e7409bbc4d2a2d32de4ee8
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04877811

Notizen zur Reaktion

Wird geladen…