Water → 3-{3-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid methyl ester

HRID 2103437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2103437
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10]Cl)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:28][C:29]1[CH:30]=[C:31]([CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH:32]=[CH:33][CH:34]=1.O>CN(C=O)C>[CH3:40][O:39][C:37](=[O:38])[CH2:36][CH2:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH2:10][C:9]2[S:8][C:7]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[N:6][C:5]=2[CH2:1][CH2:2][CH2:3][CH3:4])[CH:30]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 230893954-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

Produkt 1

HCID 578043033-{3-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid methyl esterAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole (300 mg, 0.90 mmol) in anhydrous DMF (5 mL) add cesium carbonate (586 mg, 1.80 mmol) and methyl 3-(3-hydroxyphenyl)propionate (178 mg, 0.99 mmol). Stir the resulting mixture overnight then pour into water and extract twice with ethyl acetate. Wash the combined extracts with water, dry over MgSO4, filter and concentrate under vacuum. Purify the residue by flash chromatography on silica gel (eluting with 5% ethyl acetate in heptane) to give the title compound (290 mg) as a yellow oil.

Aufarbeitung

  1. extractionextract twice with ethyl acetate
  2. washWash the combined extracts with water
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by flash chromatography on silica gel (eluting with 5% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-7c378f3cbbb14ffda35a60b676e91876
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576109B2

Notizen zur Reaktion

Wird geladen…