Oxalyl chloride → HCID 22046699, compound

Participants

Reaction Steps

A catalytic amount of DMF (5 drops) was added to a stirred solution of 124 (10 g, 30.0 mmol) and oxalyl chloride (4.65 g, 36.0 mmol) in dry CH3CN (115 mL) under a nitrogen atmosphere. The reaction mixture was allowed to stir overnight and the resulting acid chloride used directly in the next part of the procedure. 4-benzyloxy-3,5-dimethoxy-2-nitro-benzoyl chloride in anhydrous CH3CN (115 mL) was added dropwise over 0.5 hours to a stirring solution of pyrrolidine methanol (3.34 g, 33.03 mmol, 1.1 eq) and TEA (7.58 g, 75.1 mmol, 2.5 eq) in anhydrous DCM (100 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 1N 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 the solvent yielded a brown glass (8.71 g, 20.9 mmol, 70%); 1H NMR (270 MHz, CDCl3) δ1.7-2.2 (m, 4H), 3.3-3.5 (m, 2H), 3.7-3.9 (m, 2H), 3.9 (s, 3H), 4.0 (s, 3H), 4.2-4.3 (m, 1H), 5.1 (s, 2H), 6.85 (s, 1H), 7.3-7.5 (m, 5H); 13C NMR (67.8 MHz, CDCl3) δ167.3, 156.8, 148.2, 142.3, 136.4, 136.0, 129.0, 128.5, 128.4, 104.8, 75.6, 65.7, 62.8, 61.4, 56.6, 50.2, 28.3, 24.5.

Provenance & Evidence