반응 #1982350

반응 방정식

methyl 4-methoxy-3-oxobutanoate

NaOAc

2,2,6-trifluoro-1,3-benzodioxol-5-amine

NaNO2

→

title compound

수율 70.0%

Methyl 4-methoxy-3-oxo-2-[(2,2,6-trifluoro-1,3-benzodioxol-5-yl)hydrazono]butanoate

수율 70.0%

용매

EtOH

HCl

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added the above solution at 0° C
2. 2
   여과The precipitates were collected by filtration
3. 3
   세척washed with water
4. 4
   workup.DISSOLUTIONdissolved in EtOAc
5. 5
   세척washed with brine and NaHCO3 aqueous solution
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo

실험 절차

To a suspension of 2,2,6-trifluoro-1,3-benzodioxol-5-amine (4.95 g, 25.9 mmol) in 6 M HCl aqueous solution (25.9 mL) was added a solution of NaNO2 (2.15 g, 31.1 mmol) in water (5.2 mL) at 0° C. To a suspension of methyl 4-methoxy-3-oxobutanoate (3.35 mL, 25.9 mmol) and NaOAc (38.9 g) in EtOH (44 mL) was added the above solution at 0° C. The mixture was stirred at 0° C. for 10 min. The precipitates were collected by filtration, washed with water, dissolved in EtOAc, washed with brine and NaHCO3 aqueous solution, dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (6.31 g, 70% yield) as a red solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.33 (3H, s), 3.82 (3H, s), 4.66 (2H, s), 7.57-7.92 (2H, m), 12.32 (1H, brs).

출처