تفاعل #65925

معادلة التفاعل

3-Dipropylamino-5-trifluoromethanesulfonylchroman

dimethylformamide methanol

1,3-bis-diphenylphosphinopropane

triethylamine

→

3-Dipropylamino-5-methyloxycarbonylchroman

المردود 76.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solution was degassed (10 mm Hg, 20° C., 15 min)
2. 2
   درجة الحرارةThe solution was cooled
3. 3
   غسيلwashed with aqueous NaHCO3
4. 4
   تجفيفdried with Na2SO4
5. 5
   أخرىevaporated to dryness
6. 6
   أخرىThe oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8

الإجراء التجريبي

3-Dipropylamino-5-trifluoromethanesulfonylchroman (Example 1; 4.43 g, 11.6 mmol) was dissolved in 80 mL dimethylformamide/methanol 6:2 and the solution was degassed (10 mm Hg, 20° C., 15 min). PdOAc2 (76 mg, 0.34 mmol), 1,3-bis-diphenylphosphinopropane (141 mg, 0.34 mmol) and triethylamine (3.5 mL, 25 mmol) were then added. The mixture was heated to 70° C. under CO atmosphere and stirred for 5 hours. The solution was cooled, diluted with toluene (200 mL), washed with aqueous NaHCO3, dried with Na2SO4 and evaporated to dryness. The oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8. Yield: 76%, Mp 150°-152° C. (HCl-salt).

المصدر