Acetone → HCID 117728921, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Intermediate 38b (1.73 g, 6.15 mmol) in THF (40 mL) was treated with triphenyl phospine (3.22 g, 12.3 mmol) and TEA (3.43 mL, 24.6 mmol). Hexachloroethane (2.91 g, 12.3 mmol) was added to the solution portion wise over a period of 5 minutes. The reaction mixture was heated at 60° C. for 16 hours. The reaction mixture was cooled down, treated with acetone to precipitate the triethylammonium chloride, which was then filtered; the filter cake was washed abundantly with acetone and the solvent was evaporated under reduced pressure. The residue was purified by SCX-2 cartridge eluting with DCM (40 mL), MeOH (40 mL) and 2M NH3 in MeOH (40 mL). The product containing fractions were evaporated under reduced pressure to give the title compound as a brown oil (1.3 g, 80%). 1H NMR (300 MHz, d6-DMSO): 201-2.13 (1H, m), 2.2 (3H, s), 2.29 (6H, s), 2.31-2.33 (1H, m), 2.34-2.39 (1H, m), 2.51-2.61 (1H, m), 2.88-2.98 (1H, m), 3.31-3.39 (1H, dd), 3.50 (1H, s), 4.17-4.27 (1H, m), 7.14-7.24 (1H, m), 7.67-7.77 (1H, m), 9.00-9.07 (1H, m).

Provenance & Evidence