Reaktion #483585

Reaktionsgleichung

2,4-Diphenyl-oxazole-5-carboxylic acid methoxy-methyl-amide

N-BOC propargyl amine

n-BuLi

→

title compound

[4-(2,4-Diphenyl-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 (641 mg, 4.13 mmole, 3.5 eq) in dry THF (12 ml) was treated dropwise with a 1.6M n-BuLi in hexanes solution (5.16 ml, 8.3 mmole, 7.0 eq) and the resulting pale yellow dianion solution stirred at −15° C. for 30 minutes under nitrogen. A dry THF solution (3 ml) of the above-prepared 2,4-Diphenyl-oxazole-5-carboxylic acid methoxy-methyl-amide (365 mg, 1.18 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), then warmed to room temperature and extracted with ethyl acetate. The organic phase was washed with water and brine then dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a crude brown oil. The crude oil without purification was used immediately in next step.

Quelle