Triethylamine → 2,2-Dimethylpropionic acid 3-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-4-oxobicyclo[3.2.1]oct-2-en-2-yl ester

HRID 45911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45911
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:23][CH3:24])=[C:11]([CH:13]3[C:19](=[O:20])[CH:18]4[CH2:21][CH:15]([CH2:16][CH2:17]4)[C:14]3=[O:22])[N:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:23][CH3:24])=[C:11]([C:13]3[C:14](=[O:22])[CH:15]4[CH2:21][CH:18]([CH2:17][CH2:16]4)[C:19]=3[O:20][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[N:12]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 667420403-[2-(4-Chlorophenyl)-5-ethylthiazol-4-yl]bicyclo[3.2.1]octane-2,4-dione

Produkt 1

HCID 667425252,2-Dimethylpropionic acid 3-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-4-oxobicyclo[3.2.1]oct-2-en-2-yl esterAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the 3-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]bicyclo[3.2.1]octane-2,4-dione (100 mg, 0.28 mmol) in dichloromethane (5 ml) and triethylamine (140 μl, 1 mmol) is added pivaloyl chloride (123 μl, 1 mmol) at room temperature. The reaction mixture is stirred overnight at room temperature. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 2,2-dimethylpropionic acid 3-[2-(4-chlorophenyl)-5-ethylthiazol-4-yl]-4-oxobicyclo[3.2.1]oct-2-en-2-yl ester (101 mg)

Aufarbeitung

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b8062e9ea055475da6b607c9867ff932
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541594B2

Notizen zur Reaktion

Wird geladen…