Iodine → HCID 10537657, compound

Temperature

20 °C

A solution of β-mercapto-γ-butyrolactone (106 mg, 0.9 mmol) in dichloromethane (2 ml) was treated with a solution of iodine (253 mg, 1 mmol) in dichloromethane (5 ml) and the mixture was stirred for 18 h at 20° C. The reaction mixture was diluted with dichloromethane and washed with aqueous sodium metabisulfite solution, dried (MgSO4), the solvent was removed under reduced pressure, and the residue was purified by preparative TLC on a single plate (20 cm×20 cm) run in ethyl acetate-cyclohexane (2:1) to give the title compound (30 mg, 28%):. MS (TSP+ve) m/z 252 (M+NH4)+ ; IR νmax (KBr) 1778, 1771, 1164, 1023, 989, 843 cm-1 ; NMR δ (CDCl3) 4.6 (2 H, dd, J 9 and 6 Hz), 4.35 (2 H, dt, J 5 and 4 Hz), 3.86-3.72 (2 H, m), 2.96 (2 H, dd, J 17 and 8 Hz), 2.66 (2 H, dt, J 18 and 5 Hz); HRMS (EI) found: 234.0017. C8H10O4S2 requires 234.0020.

1. washwashed with aqueous sodium metabisulfite solution
2. dry with materialdried (MgSO4)
3. customthe solvent was removed under reduced pressure
4. customthe residue was purified by preparative TLC on a single plate (20 cm×20 cm) run in ethyl acetate-cyclohexane (2:1)

ORD record

ord-d7036dced8b84d1fb050906ceee32eac

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06114318