تفاعل #90664

معادلة التفاعل

CH3CN CO2

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

N-methoxy-N-methylacetamide

isopropylmagnesium chloride

→

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

المردود 71.1%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise via
2. 2
   workup.STIRRINGThe reaction was stirred for 2 hr (
3. 3
   أخرىquenched with aq. NH4Cl
4. 4
   استخلاصextracted with EtOAc
5. 5
   غسيلwashed with brine
6. 6
   تجفيفdried (Na2SO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated to dryness under vacuum
9. 9
   أخرىThe remaining was purified by silica gel chromatography (Analogix
10. 10
    أخرىevaporated to dryness

الإجراء التجريبي

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 evaporated 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]+.

المصدر