Sodium Bromide → HCID 11229211, compound

Participants

Reaction Steps

An aqueous NaOCl solution (11 mmol, 5.3 ml of a 12.5% solution) and NaHCO3 (2.43 g, 29 mmol) was added dropwise, over a period of 1 hour, to a cold (0° C.), rapidly stirred (>1000 rpm), biphasic mixture consisting of (2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol (5) (1.88 g, 10 mmol), TEMPO with free radicals (31.25 mg, 2%), sodium bromide (1.029 g, 10 mmol), toluene (30 ml), EtOAc (30 ml) and H2O (5 ml). The aqueous phase was separated and washed with Et2O (50 ml). The combined organic phases were washed with a KI solution (80 mg) dissolved in aqueous 10% KHSO4 (20 ml), and then with a 10% aqueous sodium thiosulfate solution (10 ml), brine (20 ml), and dried (MgSO4). Filtration and concentration under vacuum gave the desired aldehyde 6 (1.72 g, 92%) which was used for the next reactions without further purification.

Provenance & Evidence