Methyl bromoacetate → Methyl [3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenoxy]acetate

HRID 1461755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461755
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>C(#N)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[O:26][CH2:28][C:29]([O:31][CH3:32])=[O:30])[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 60984Methyl bromoacetateHCID 150069043-[2-(4,5-Diphenyl-2-thiazolyl)ethyl]phenol

Produkt 1

HCID 10477744Methyl [3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenoxy]acetateAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-[2-(4,5-diphenyl-2-thiazolyl)-ethyl]phenol (3.65 g, 10 mmol), methyl bromoacetate (1.72 g, 1.06 mL, 11 mmol) potassium carbonate (1.69 g, 12 mmol) and acetonitrile (60 mL) was stirred at reflux for 90 minutes. The mixture was filtered and concentrated to leave an oil which was subjected to chromatography on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (2:1) afforded methyl [3-[2-(4,5-diphenyl-2-thiazolyl)-ethyl]phenoxy]acetate (3.63 g, 82%) as an oil.

Aufarbeitung

  1. temperatureat reflux for 90 minutes
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customto leave an oil which
  5. washElution
  6. additionwith a mixture of hexanes and diethyl ether (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f036c1e836474b0b806e690e6087d578
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05077305

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