Thiophenol → HCID 45381115, compound

Participants

Reaction Steps

Compound 52 (4.11 g, 8.58 mmol) was dissolved under reflux in a mixture of CH3CN (150 mL) and methanol (50 mL). Then, Cs2CO3 (8.4 g, 25.78 mmol) was added and at once PhSH (2.6 mL, 25.48 mmol) was poured in. The resulting mixture was refluxed for 2.5 h (TLC monitoring, eluent: chloroform-methanol, 9:1) and evaporated to dryness. Then, water and a solution of HCl were added. As a result, all the solid products were dissolved. The acidic aqueous solution was extracted with ethyl acetate until the latter ceased to become yellow. The aqueous layer was neutralized with a saturated solution of NaHCO3, extracted with a CH2Cl2-MeOH mixture (4:1), and the extract was evaporated. The residue was washed off with MeCN and washed with ether. Yield of 53: 1.25 g (50%) as beige crystals.

Provenance & Evidence