Реакция #80543

Уравнение реакции

(R)-8-Fluoro-3-(N-isopropyl-N-n-propylamino)-5-trifluoromethanesulfonyloxy-3,4-dihydro-2H-1-benzopyran

triethylamine

DMF MeOH

→

title compound

Выход 71.0%

Methyl (R)-8-fluoro-3-(N-isopropyl-N-n-propylamino)-3,4 -dihydro-2H-1-benzopyran-5-carboxylate

Выход 71.0%

Условия реакции

Обработка

1. 1
   ДругоеThe flask was evacuated
2. 2
   ДругоеThe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in diethyl ether/
4. 4
   ДругоеThe layers were separated
5. 5
   Экстракцияthe water phase was extracted once with ether
6. 6
   СушкаThe combined ether layers were dried (MgSO4)
7. 7
   Другоеthe solvent was removed in vacuo
8. 8
   Другоеto give a crude which
9. 9
   Другоеwas purified by flash chromatography (SiO2, hexane/EtOAC, 9:1)

Методика

(R)-8-Fluoro-3-(N-isopropyl-N-n-propylamino)-5-trifluoromethanesulfonyloxy-3,4-dihydro-2H-1-benzopyran (2.4 g, 6.0 mmol), triethylamine (1.3 g, 12.9 mmol), 1,3-bis (diphenylphosphino)propane (95 mg, catalytic amount), palladium(II)acetate (48 mg, catalytic amount) and DMF/MeOH (30 mL, 3:1) were mixed in a 50 mL three necked round bottom flask. The flask was evacuated followed by the inlet of CO (repeated two times). The reaction mixture was stirred at 70° C. for 7.5 hours. The solvent was removed in vacuo and the residue was dissolved in diethyl ether/sat. NaHCO3. The layers were separated and the water phase was extracted once with ether. The combined ether layers were dried (MgSO4) and the solvent was removed in vacuo to give a crude which was purified by flash chromatography (SiO2, hexane/EtOAC, 9:1) to give 1.3 g of the title compound (71% yield).

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