Reaktion #483580

Reaktionsgleichung

4-methyl-2-phenyl-oxazole-5-carboxylic acid methoxy-methyl-amide

N-BOC propargyl amine

n-BuLi

→

title compound

[4-(4-Methyl-2-phenyl-oxazol-5-yl)-4-oxo-but-2-ynyl]-carbamic Acid Tert-butyl Ester

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred at 0° C. for 2 hours under nitrogen
2. 2
   SonstigeThe mixture was quenched
3. 3
   workup.ADDITIONby adding a solution of 2M NaH2PO4 (5 ml)
4. 4
   Temperaturwarmed to room temperature
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   WaschenThe organic phase was washed with water and brine
7. 7
   Trocknenthen dried over anhydrous sodium sulfate
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A −15° C. solution of N-BOC propargyl amine (651 mg, 4.2 mmole, 3.5 eq) in dry THF (12 ml) was treated dropwise with a 1.6M n-BuLi in hexanes solution (5.25 ml, 8.4 mmole, 7.0 eq) and the pale yellow dianion solution was stirred at −15° C. for 30 minutes under nitrogen. A dry THF solution (3 ml) of the above-prepared 4-methyl-2-phenyl-oxazole-5-carboxylic acid methoxy-methyl-amide (296 mg, 1.2 mmole, 1.0 eq) was added dropwise to the dianion solution at −15° C. and the mixture stirred at 0° C. for 2 hours under nitrogen. The mixture was quenched by adding a solution of 2M NaH2PO4 (5 ml), warmed to room temperature, and then extracted with ethyl acetate. The organic phase was washed with water and brine then dried over anhydrous sodium sulfate and concentrated in vacuo to provide the title compound as a crude brown oil. The crude oil was used immediately in the next step without further purification.

Quelle