反应详情

A catalytic amount of DMF (2 drops) was added to a stirred solution of 189 (3.96 g, 15.32 mmol) and oxalyl chloride (2.14 g, 16.85 mmol) in dry CH2Cl2 (50 mL) under a nitrogen atmosphere. The reaction mixture was allowed to stir overnight and the resulting acid chloride used directly in the next stage of the procedure. 4-methyl-3,5-dimethoxy-2-nitro-benzoyl chloride in anhydrous DCM (50 mL) was added dropwise over 0.5 hours to a stirring solution of pyrrolidine methanol (1.55 g, 15.32 mmol, 1.1 eq) and TEA (3.87 g, 38.3 mmol, 2.5 eq) in anhydrous DCM (50 mL) at 0° C. under a nitrogen atmosphere and the reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was washed with 1 N HCl (2×100 mL), and the organic layer was washed with distilled H2O (2×100 mL), brine (2×100 mL) and dried over anhydrous MgSO4. Evaporation of excess solvent yielded a yellow glass (190) (2.13 g, 6.56 mmol, 43% -2 steps); 1H NMR (270 MHz, CDCl3) δ6.61 (s, 1H), 4.30-4.28 (m, 1H), 3.91 (s, 3H), 3.89 (s, 3H), 3.83-3.68 (m, 2H), 3.46-3.26 (m, 2H), 2.19 (s, 3H), 1.94-1.68 (m, 4H); 13C NMR (67.8 MHz, CDCl3) δ167.85, 161.15, 152.62, 135.70, 132.32, 123.17, 103.70, 65.87, 62.61, 61.37, 56.36, 50.20, 28.41, 24.50, 9.34.

1. stirringto stir overnight at room temperature
2. washThe reaction mixture was washed with 1 N HCl (2×100 mL)
3. washthe organic layer was washed with distilled H2O (2×100 mL), brine (2×100 mL)
4. dry with materialdried over anhydrous MgSO4
5. customEvaporation of excess solvent