Iodine → HCID 25009592, compound

Participants

Reaction Steps

To a solution of iodine (107.2 mg, 0.42 mmol) in CH2Cl2/MeOH (9:1, 143 mL) was added dropwise a solution of 6B (48.4 mg, 0.0041 mmol) in CH2Cl2/MeOH (9:1) (70 mL) over 30 min, the reaction mixture was then allowed to stir for a further 30 min after which time sodium thiosulfate (26 mL, 0.05 M) was added. The organic phase was separated and the aqueous phase extracted with CH2Cl2 (3×20 mL). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography on silica gel (eluent 0:100-1:99-3:97 MeOH/CH2Cl2) which gave 7B (13 mg, 0.019 mmol, 46%) as a white solid: Rf 0.18 CH2Cl2/MeOH (97:3); [α]28D=−1.9 (c 0.36, CHCl3); IR (thin film) 3379 (br), 3343 (br), 2974 (m), 2931 (m), 1732 (s), 1662 (s), 1538 (m), 1519 (m), 1453 (m), 1371 (s), 1333 (m), 1310 (m), 1271 (m), 1255 (s).

Provenance & Evidence