Dimethyl Sulfoxide → HCID 118413482, compound

Participants

Reaction Conditions

Reaction Steps

Compound 6 (5.434 g, 33.9 mmol) was added to a stirring solution of anhydrous DMSO (30 mL) and powdered KOH (7.6 g, 135.7 mmol). After stirring for 10 minutes, the reaction mixture was cooled in an ice bath (0° C.). Propargyl bromide (4.04 g, 3.02 mL, 33.93 mmol) was added drop-wise, the reaction became dark brown rapidly. The reaction was stirred at room temperature for 95 minutes and poured into ice-cold water (200 mL). The product, an off-white solid, was collected by vacuum filtration, and washed with water, dried in vacuo to obtain the analytically pure product. X-ray quality crystals were obtained by slow evaporation from chloroform. Yield: 81%, 5.44 g. 1H NMR (CDCl3; 500 MHz) δ ppm: 1.456 (s, 3H, CH3), 2.442 (t, 1H, CCH), 3.286 (s, 2H, CCH2O), 4.006 (s, 6H, (CH2)3C), and 4.094 (d, 2H, OCH2CCH). 13C NMR (CDCl3; 125.8 MHz) δ ppm: 23.56 (CH3), 34.85 (CH2CCH2), 58.88 (OCH2CCH), 68.12 (CCH2O), 69.55 (OCH2C), 75.34 (CH), 78.97 (CH2CCH), 108.72 (OCCH3). ESI-MS (m/z): 199.10 (199.09 calc'd for C10H14O4 [M+H]+). Elemental analysis calc'd (found) for C7H12O4: C, 60.59 (59.06); H, 7.12 (7.23).

Provenance & Evidence