반응 #1892707

반응 방정식

methyl 4-methoxy-3-oxobutanoate

NaOAc

2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-amine

NaNO2

→

title compound

수율 85.0%

Methyl 4-methoxy-3-oxo-2-[(2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)hydrazono]butanoate

수율 85.0%

용매

EtOH

HCl

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added the above solution at 0° C
2. 2
   workup.STIRRINGThe mixture was stirred at 0° C. for 15 min
3. 3
   여과The precipitates were collected by filtration
4. 4
   세척washed with water
5. 5
   workup.DISSOLUTIONdissolved in EtOAc
6. 6
   세척washed with brine
7. 7
   건조dried over MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo

실험 절차

To a suspension of 2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-amine (4.87 g, 20.2 mmol) in 6 M HCl aqueous solution (20.2 mL) was added a solution of NaNO2 (1.67 g, 24.2 mmol) in water (4 mL) at 0° C. The mixture was stirred at 0° C. for 15 min. To a suspension of methyl 4-methoxy-3-oxobutanoate (2.61 mL, 20.2 mmol) and NaOAc (30.3 g) in EtOH (34 mL) was added the above solution at 0° C. The mixture was stirred at 0° C. for 15 min. The precipitates were collected by filtration, washed with water, dissolved in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (6.84 g, 85% yield) as a red solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.33 (3H, s), 3.82 (3H, s), 4.68 (2H, s), 7.66-7.93 (2H, m), 12.16 (1H, brs).

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