反应详情

To a 20 mL round-bottomed flask equipped with reflux condenser and drying tube was added 4-tert-butyl-trans-cinnamic acid (200 mg, 0.98 mmol, EMKA-Chemie) followed by CH2Cl2 (5 mL), oxalyl chloride (90 uL, 130 mg, 1.03 mmol, Aldrich) and DMF (1 uL). The reaction mixture was magnetically stirred and heated at reflux for 30 min. The reaction mixture was concentrated in vacuo and the residue dissolved in acetone (2 mL). The solution was added to a mixture of 3,4-dimethoxyaniline (180 mg, 1.17 mmol, Aldrich), potassium carbonate (200 mg), water (2 mL) and acetone (2 mL), magnetically stirred at 25° C. in a 10 mL glass vial. The reaction mixture was stirred at 25° C. for 16 h then diluted with EtOAc (60 mL) and washed successively with 1 N HCl (20 mL), 1 N NaOH (20 mL), water (20 mL) and satd NaCl (20 mL), dried over MgSO4, filtered and concentrated. Recrystallization from hexane and CH2Cl2 provided the title product as a yellow solid. MP 115-116° C. MS (ESI, pos. ion) m/z: 340 (M+1).

1. customTo a 20 mL round-bottomed flask equipped
2. temperaturewith reflux condenser
3. customdrying tube
4. temperatureheated
5. temperatureat reflux for 30 min
6. concentrationThe reaction mixture was concentrated in vacuo
7. dissolutionthe residue dissolved in acetone (2 mL)
8. stirringThe reaction mixture was stirred at 25° C. for 16 h
9. washwashed successively with 1 N HCl (20 mL), 1 N NaOH (20 mL), water (20 mL) and satd NaCl (20 mL)
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customRecrystallization from hexane and CH2Cl2