Hydrochloric Acid → 1-(4-methyl-thiazol-2-yl)-cyclopropanecarboxylic Acid Ethyl Ester

HRID 1697700

Reaktionsgleichung

Reaktionsgleichung von HRID 1697700
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:5][CH:6]=1.Br[CH2:14][CH2:15]Br.C([O-])([O-])=O.[Cs+].[Cs+].Cl>CN(C=O)C>[CH2:11]([O:10][C:8]([C:7]1([C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH2:15][CH2:14]1)=[O:9])[CH3:12]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 574575Ethyl 2-(4-methyl-1,3-thiazol-2-yl)acetate

Produkt 1

HCID 667709321-(4-methyl-thiazol-2-yl)-cyclopropanecarboxylic Acid Ethyl EsterAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl 2-(4-methylthiazol-2-yl)acetate (1 g, 5.4 mmol, Eq: 1.00) was dissolved in DMF (5 mL). 1,2-dibromoethane (1.62 g, 744 μL, 8.64 mmol, Eq: 1.60) and Cs2CO3 (4.4 g, 13.5 mmol, Eq: 2.50) were added. The reaction mixture was stirred 48 h at RT. The reaction mixture was poured into 0.5 M aqueous HCl (100 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered and evaporated. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 50% EtOAc in heptane) to yield 1.14 g (73.6%) of a light yellow liquid. MS (ESI): m/z=212.0 [M+H]+.

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by flash chromatography (silica gel, 50 g, 0% to 50% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-8f4ea559448f47c8bbc435385e9194b6
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163793B2

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