Trifluoroacetic acid → 5-(4-Chloro-2-methoxybenzyl)-1,3-thiazole

HRID 272747

Reaktionsgleichung

Reaktionsgleichung von HRID 272747
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)O)=[C:4]([O:15][CH3:16])[CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:10]2[S:14][CH:13]=[N:12][CH:11]=2)=[C:4]([O:15][CH3:16])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69219630(4-Chloro-2-methoxyphenyl)(1,3-thiazol-5-yl)methanol

Produkt 1

HCID 692195725-(4-Chloro-2-methoxybenzyl)-1,3-thiazoleAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of Example 679A (204 mg, 0.8 mmol), trifluoroacetic acid (0.87 mL, 8 mmol), and triethylsilane (1.27 mL, 8 mmol) in methylene chloride was stirred at room temperature for 5 days. The solution was concentrated under vacuum, diluted with methylene chloride, and poured into 2M NaOH. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was then purified by flash column chromatography on silica gel with 1:1 hexanes/methylene chloride to provide 108 mg (57%) of the title compound. MS (ESI) m/e 240 (M+H)+, 1H NMR (DMSO-d6, 300 MHz): □ 8.88 (s, 1H), 7.67 (s, 1H), 7.21 (d, J=7.80 Hz, 1H), 7.07 (d, J=2.03 Hz, 1H), 6.96 (dd, J=7.80, 2.03 Hz, 1H), 4.10 (s, 2H), 3.84 (s, 3H).

Aufarbeitung

  1. concentrationThe solution was concentrated under vacuum
  2. additiondiluted with methylene chloride
  3. additionpoured into 2M NaOH
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was then purified by flash column chromatography on silica gel with 1:1 hexanes/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-b5010b193b024a81943eb88a27c9a20e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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