Dimethyl Sulfoxide → HCID 87579254, compound

Participants

Reaction Steps

A solution of oxalyl chloride (14.2 mL, 165.5 mmol, Spectrochem) in DCM (30 mL) was cooled to −78° C. and was added DMSO (21.1 mL, 298 mmol, Spectrochem) drop wise. The reaction mixture was stirred for 20 minutes at the same temperature and a solution of rac ((2S*,5S*)-5-(hydroxymethyl)-1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate (20 g, 66.2 mmol, Preparation #11: Step c) in DCM (60 mL) was added slowly. The reaction mixture was stirred at the same temperature for another 1 h and quenched with TEA (26.7 mL, 364.2 mmol). The reaction mixture was warmed to RT, diluted with DCM (50 mL) and washed successively with 1N HCl (2×150 mL), saturated sodium bicarbonate (2×100 mL) and brine (2×100 mL). The organic layer was dried over sodium sulphate and evaporated to dryness under reduced pressure to afford racemnic ((2S*,5R*)-5-formyl-1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate 20 g (crude, 100%); 1H NMR (400 MHz, CDCl3): δ 9.55 (s, 1H), 7.80 (d, J=8.4 Hz, 2H), 7.37 (d, J=7.6 Hz, 2H), 4.01-3.92 (m, 5H), 3.76 (m, 1H), 3.53-3.42 (m, 2H), 2.45 (s, 3H); MS m/z: 301.3 (m+H)+

Provenance & Evidence