Triethylamine → HCID 11045242, compound

Participants

Reaction Conditions

Reaction Steps

To a round-bottomed flask (100 mL) equipped with magnetic stir bar and addition funnel (10 mL) was charged 1b (3.0 g, 16.5 mmol), CH2Cl2 (50 mL) and triethylamine (3.3 g, 33 mmol, 2 equiv). The mixture was cooled to 0° C. in an ice bath. The funnel was charged with Tf2O (6.9 g, 4.18 mL, 24.8 mmol, 1.5 equiv) which was added dropwise over 1 h. After several hours at 0° C., the mixture was allowed to warm up to room temperature and washed with H2O. The organic phase was washed with brine (25 mL), separated and dried over anhydrous MgSO4. The organic phase was treated with decolorizing charcoal, filtered and evaporated under reduced pressure. Compound 2b was obtained as colorless crystals by recrystallization from hexanes (4.5 g, 87%), mp. 105-107° C., lit.21 108-110° C. 1H NMR (CDCl3): δ 9.95 (s, 1H), 7.17 (s, 2H), 3.99 (s, 6H); 13C NMR (CDCl3): δ 190.65, 153.45, 136.13, 132.25, 118.85 (q, 1JCF=321.2 Hz), 106.15, 56.89; 19F {13C} NMR (CDCl3): δ −74.08. Anal. Calcd for C10H9F3O6S: C, 38.22; H, 2.89. Found: C, 38.43; H, 2.89.

Provenance & Evidence