Thiophenol → HCID 15511970, compound

Temperature

-78 °C

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).

1. customThe layers were separated
2. washthe organic layer was washed with 2×100 mL of saturated NaHCO3, 100 mL of water and 100 mL of brine
3. dry with materialThe organic layer was dried over anhydrous MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customto afford a yellow liquid
7. customcrystallization
8. customWhite powdery solid formed which
9. filtrationwas filtered off
10. washwashed with cold ether

ORD record

ord-6d22411bb0164d47b21683f4a70a7966

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05994397