Thiophenol → HCID 21253503, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7 (35.7 g, 0.11 mol) and thiophenol (14.8 mL, 0.13 mol) in 220 mL of a 4:1 mixture of anhydrous toluene and dichloromethane at room temperature, boron trifluoride etherate (6.9 mL, 0.05 mol) was added dropwise. The resulting mixture was stirred at the same temperature for 6.5 h and then carefully poured into a biphasic mixture of 1000 mL of EtOAc and 100 mL of a saturated aqueous solution of NaHCO3 (sat. NaHCO3). The layers were separated and the organic layer was washed with 2×100 mL of saturated NaHCO3, 100 mL of water and 100 mL of brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to afford a yellow liquid. This material was dissolved in 50 mL of CHCl3, and to it was added 200 mL of ether and 50 mL of hexane. The resulting solution was briefly cooled to -78° C. to induce crystallization. White powdery solid formed which was filtered off and washed with cold ether to afford 29.6 g of 8 (72% yield) as a mixture of two diastereomers: Rf 0.70 and 0.53 (minor and major isomers, respectively, 60% EtOAc/hexane); 1H-NMR (CDCl3) δ (for major isomer only) 8.01 (m, 2H), 7.42-7.70 (m, 5H), 7.27 (m, 3H), 5.89 (d, 1H, J=5.2 Hz), 5.29 (dd, 1H, J=7.7, 5.2 Hz), 4.55 (m, 2H), 4.48 (m, 1H), 2.60-3.12 (m, 3H).

Provenance & Evidence