Sodium Bromide → HCID 11229211, compound

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.

1. customThe aqueous phase was separated
2. washwashed with Et2O (50 ml)
3. washThe combined organic phases were washed with a KI solution (80 mg)
4. dissolutiondissolved in aqueous 10% KHSO4 (20 ml)
5. dry with materialwith a 10% aqueous sodium thiosulfate solution (10 ml), brine (20 ml), and dried (MgSO4)
6. filtrationFiltration and concentration under vacuum

ORD record

ord-1cbe211bd93e4e9d9245898edb35a9aa

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07432087B2