반응 #987617

반응 방정식

4-Methylpyrimidine

Lithium diisopropylamide

N-methoxy-N-methylacetamide

→

(4-Pyrimidyl)acetone

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred at −78° C. for a further 40 minutes
2. 2
   온도to warm to room temperature over 1.25 h
3. 3
   기타partitioned between saturated aqueous sodium carbonate and ethyl acetate
4. 4
   기타The layers were separated
5. 5
   추출the aqueous phase further extracted with ethyl acetate
6. 6
   세척The combined extracts were washed with brine
7. 7
   건조dried (MgSO4)
8. 8
   여과filtered
9. 9
   기타evaporated
10. 10
    기타The residue was purified by column chromatography on silica gel eluting with 40-50% ethyl acetate in hexane
11. 11
    기타to give an oil which
12. 12
    기타crystallised

실험 절차

4-Methylpyrimidine (2 g) was stirred in dry tetrahydrofuran (65 ml) under argon and the solution was cooled to −78° C. Lithium diisopropylamide (13.8 ml, 2M solution) was added dropwise over 20 minutes and stirring was continued at −78° C. for 1.5 h before dropwise addition of N-methoxy-N-methylacetamide (2.49 ml). The reaction mixture was stirred at −78° C. for a further 40 minutes before allowing to warm to room temperature over 1.25 h, then partitioned between saturated aqueous sodium carbonate and ethyl acetate. The layers were separated and the aqueous phase further extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel eluting with 40-50% ethyl acetate in hexane to give an oil which crystallised on standing (0.70 g, 24%).

출처