반응 #70765

반응 방정식

CH3CN CO2

4-(2-propyn-1-yl)morpholine

N-methoxy-N-methylacetamide

isopropylmagnesium chloride

→

5-(4-morpholinyl)-3-pentyn-2-one

수율 71.1%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise via
2. 2
   workup.STIRRINGThe reaction was stirred for 2 hr (
3. 3
   기타quenched with aq. NH4Cl
4. 4
   추출extracted with EtOAc
5. 5
   세척washed with brine
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   기타The remaining was purified by silica gel chromatography (Analogix
9. 9
   기타evaporated to dryness

실험 절차

To a cooled (−40° C., CH3CN/CO2) solution of 4-(2-propyn-1-yl)morpholine (2.2 g, 17.58 mmol) in THF (5 mL) was added dropwise via. syringe under N2 a solution of 2 M isopropylmagnesium chloride in THF (10 mL, 20.00 mmol). The reaction was stirred for 1 hr then a solution of N-methoxy-N-methylacetamide (2.2 mL, 20.69 mmol) in THF (5 mL) was added in one portion. The reaction was stirred for 2 hr (allowed to slowly warm to RT), quenched with aq. NH4Cl, extracted with EtOAc, washed with brine, dried (Na2SO4), filtered and evaoprated to dryness under vacuum. The remaining was purified by silica gel chromatography (Analogix, SF25-60 g, 0 to 80% EtOAc in hexanes). The pure fractions were combined and evaporated to dryness to give the product 5-(4-morpholinyl)-3-pentyn-2-one (2.09 g, 12.50 mmol, 71.1% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 3.62-3.57 (m, 4H), 3.56 (s, 2H), 2.49-2.43 (m, 4H), 2.34 (s, 3H). MS (ES)+m/e 168.0 [M+H]+.

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