5-氨基-2,2-二甲基-3H-色烯-4-one

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a 100 mL round bottom flask equipped with a magnetic stir bar was added 6 (234 mg, 1.23 mmol), benzyltriethylammonium dichloroiodate (11, 480 mg, 1.23 mmol), sodium bicarbonate (113 mg, 1.35 mmol), CH2Cl2 (5 mL) and reagent grade methanol (2 mL). The flask was equipped with a water condenser, and the mixture was heated to 40° C. with stirring until all of compound 6 was consumed, as determined by TLC analysis. CH2Cl2 (10 mL) and 10% aqueous sodium bisulfite (10 ml) were added, the organic phase was washed with brine (1×10 mL), dried over MgSO4, filtered, concentrated and dried under high vacuum. The dry, crude product was passed through a silica gel column using straight CH2Cl2 (Rf=0.5) as eluent. The reaction provided 171 mg (44%) of 7 as a yellow solid. 1H NMR (300 MHZ, CDCl3): δ 7.58 (d, J=9 Hz, 1H), 6.00 (d, J=9 Hz, 1H), 2.67 (s, 2H), 1.40 (s, 6H). 13C NMR (75.5 MHZ, CDCl3): δ 193.9, 161.3, 149.6, 145.4, 106.9, 105.8, 78.2, 73.6, 48.8, 26.5. HRMS (EI+): calculated for C11H12INO2 [M+] m/z 316.9913, found 316.9906. To a 100 mL round bottom flask equipped with a magnetic stir bar The flask was equipped with a water condenser was consumed CH2Cl2 (10 mL) and 10% aqueous sodium bisulfite (10 ml) were added the organic phase was washed with brine (1×10 mL) dried over MgSO4 filtered concentrated dried under high vacuum