Sodium Sulfide → HCID 86585913, compound

Participants

Reaction Steps

To a stirred solution of the bis mesylate (from step 4) (5.0 g, 10.6 mmol) in dry DMSO (72 mL) is added anhydrous sodium sulfide (2.48 g, 31.8 mmol). The reaction mixture is stirred at RT for 1 h. The reaction mixture is partitioned between H2O (250 mL) and ethyl acetate (250 mL). The phases are separated, the aqueous phases is extracted with ethyl acetate (3×200 mL). The combined organic phases are dried (MgSO4), filtered and concentrated. The residue is dissolved in CH2Cl2, absorbed onto silica gel and is purified on a Biotage 40M column with SIM using 10-20% ethyl acetate in hexane as the eluent to afford 2.37 g (7.6 mmol, 71%) of the desired product as a white solid. mp 118-120° C.

Provenance & Evidence