Trifluoroacetic acid → Methyl 4-(thiazol-2-ylmethyl)benzoate

HRID 410462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410462
O[CH:2]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl.C1(C)C=CC=CC=1>[S:14]1[CH:15]=[CH:16][N:17]=[C:13]1[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12017830Methyl 4-(hydroxy(thiazol-2-yl)methyl)benzoate

Produkt 1

HCID 67249380Methyl 4-(thiazol-2-ylmethyl)benzoateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

The product of Step 1 (4.00 g, 16.05 mmol) was taken up in DCE (80 ml) with triethylsilane (25.6 ml, 160 mmol), and trifluoroacetic acid (24.72 ml, 321 mmol) was added. The reaction was stirred at reflux overnight. The reaction was diluted with toluene and evaporated to dryness. The residue was taken back up in EtOAc, washed with aqueous saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated. Flash chromatography (0-50% EtOAc/hexanes) afforded methyl 4-(1,3-thiazol-2-ylmethyl)benzoate (3.13 g, 13.42 mmol, 84% yield) as a pale yellow gum that crystallized upon standing. MS ESI: [M+H]+ m/z 234.1.

Aufarbeitung

  1. additionwas added
  2. temperatureat reflux overnight
  3. customevaporated to dryness
  4. washwashed with aqueous saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-03548a5e592b4fd59af91d505735192b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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