反应详情

To a round-bottomed flask equipped with magnetic stirring was added 4-tert-butyl-trans-cinnamic acid (530 mg, 2.43 mmol, EMKA-Chemie), CH2Cl2 (10 mL), and DMF (10 uL, Aldrich) under N2. The solution was treated dropwise with oxalyl chloride (3.0 mL, 6.0 mmol, 2.0 M in CH2Cl2, Aldrich) then stirred at 25° C. for 1 h. The reaction mixture was concentrated in vacuo and treated with 3-aminophenol (265 mg, 2.43 mmol, Aldrich), THF (20 mL) and satd K2CO3 (15 mL). The reaction mixture was stirred at 25° C. overnight, then acidified to pH˜4.5 with 1 N HCl. The mixture was extracted with EtOAc (2×30 mL), the combined organic extract was dried and concentrated in vacuo. Purification by silica gel chromatography (2:1 hexane:EtOAc) provided the title product as an oil. MS (ESI, pos. ion) m/z: 296 (M+1).

1. customTo a round-bottomed flask equipped
2. stirringthen stirred at 25° C. for 1 h
3. concentrationThe reaction mixture was concentrated in vacuo
4. stirringThe reaction mixture was stirred at 25° C. overnight
5. extractionThe mixture was extracted with EtOAc (2×30 mL)
6. extractionthe combined organic extract
7. customwas dried
8. concentrationconcentrated in vacuo
9. customPurification by silica gel chromatography (2:1 hexane:EtOAc)