Dimethyl Sulfoxide → HCID 23657705, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (2 M solution in CH2Cl2, 40 mL, 80 mmol) was placed under Ar into a reaction flask, equipped with addition funnel, inlet thermometer and drying tube charged with Drierite, and cooled to −70° C. A mixture of DMSO (12.2 mL, 171.2 mmol) and dry CH2Cl2 (30 mL) was added dropwise. After 30 min a solution of 95 (14.3 g, 61 mmol) in CH2Cl2 was slowly added and the mixture was stirred at −70° C. for 60 min. After that time triethylamine (45.2 mL, 405 mmol) was added dropwise at −60° C. The mixture was allowed to warm to room temperature, water (100 mL) was added carefully and the stirring continued for 10 min. Organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×75 mL). Combined organic were washed with 2 M HCl (30 mL), dried over Na2SO4 and concentrated. Column chromatography (SiO2, EtOAc/hexanes, 5/1) followed by recrystalliztion (EtOAc/hexanes, 1/3) afforded 97 as light yellow crystals (12.93 g, 91%): mp. 48-49° C. 1H NMR (DMSO-d6) δ9.70 (s, 1H), 8.20 (s, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.62 (d, J=8.2 Hz, 1H), 6.75 (s, 1H), 3.87 (s, 3H), 3.07 (m, 2H), 2.96 (m, 2H). Anal. (C13H12O4.0.1H2O) C, H.

Provenance & Evidence