تفاعل #65956

معادلة التفاعل

(R)-8-Fluoro-3-(N-isopropyl,N-propylamino)-5-trifluoromethanesulfonyloxychroman

triethylamine

DMF MeOH

→

title compound

المردود 71.0%

(R)-8-Fluoro-5-methoxycarbonyl-3-(N-isopropyl,N-propylamino)chroman

المردود 71.0%

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

(R)-8-Fluoro-3-(N-isopropyl,N-propylamino)-5-trifluoromethanesulfonyloxychroman (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).

المصدر