Triethylsilane → Methyl 3-benzylbenzoate

HRID 2184325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184325
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1

Komponenten

5

Edukt 2

HCID 12052TriethylsilaneHCID 349621Methyl 3-benzoylbenzoate

Produkt 1

HCID 597640Methyl 3-benzylbenzoateAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-benzoyl-benzoic acid methyl ester (653 mg, 2.72 mmol) was stirred in trifluoroacetic acid (3 mL) with triethylsilane (1.3 mL, 8.15 mmol) at room temperature for 22 h. The reaction mixture was diluted with ethyl acetate and washed with an aqueous NaHCO3 solution. The organic layer was dried over MgSO4, filtered and concentrated. The resultant oil was subjected to column chromatography (25 hexanes: 1 ethyl acetate) to provide 3-benzyl-benzoic acid methyl ester (589 mg, 2.6 mmol) as an oil.

Aufarbeitung

  1. washwashed with an aqueous NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0a49c6d055fd464e83fa1b3f726d470d
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900336B2

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