Iodine → HCID 24853065, compound

Participants

Reaction Steps

The alkene (Example 22D, 23 mg, 55 μmol) and tetrabutylammonium chloride (1.2 mg, 4 μmol) were dissolved into acetic acid (500 μL) and treated with 1 M iodine monochloride (110 μL, 110 μmol) in CH2Cl2, dropwise over 1 minute. After 15 minutes, cesium carbonate (18 mg, 55 μmol) was added. After another 10 minutes, solid NaHSO3 (16 mg, 150 μmol) was added, and the resulting suspension was thoroughly stirred until the deep iodine color had changed to a light orange (15 minutes). The suspension was diluted with CH2Cl2, stirred for 2 minutes, and filtered through a glass-fritted funnel with a CH2Cl2 rinse. The filtrate was concentrated, concentrated twice from EtOAc, dissolved into 20% EtOAc/CH2Cl2, and filtered through a pad of Aldrich basic alumina (activated, Brockmann 1, ˜150 mesh, CAS #1344-28-1) with a 20→50% EtOAc/CH2Cl2 rinse. The intermediate mixture was concentrated to 13 mg, dissolved into MeOH (500 μL), and treated with 1 M aqueous Cs2CO3 (30 μL). After ˜15 minutes, the mixture was concentrated and partitioned between CH2Cl2 and pH 7 potassium phosphate buffer. The aqueous phase was separated and extracted with CH2Cl2, and the combined organic phases were dried (Na2SO4), concentrated, and chromatographed through silica (20% EtOAc/CH2Cl2, then 5% MeOH/CH2Cl2) to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.86 (4H), 3.44 (4H), 4.65 (2H), 6.89 (1H), 7.23 (1H), 7.37 (1H), 7.48 (1H); MS (ESI) m/z 434 (M+H)+.

Provenance & Evidence