Sodium Chloride → HCID 86746644, compound

Participants

Reaction Steps

Nitrosyl chloride, prepared from sodium chloride and nitrosyl sulfuric acid, was passed into methylene chloride (7 ml) at 0° C., until a burgundy colour had developed. The solution was added in one action to 3,3-ethylenedioxypregna-5,17(20)-dien-9α-ol (301 mg). The reaction mixture was stirred for 3 minutes after which the solvents were evaporated under reduced pressure. The residue was taken up in a mixture of tetrahydrofuran (15 ml) and water (1.5 ml). Triethylamine (1.6 ml) was added dropwise, then the mixture was refluxed for 2 hours. After cooling to room temperature, methylene chloride (100 ml) was added and the mixture was washed twice with a 5% aqueous potassium carbonate solution, dried (MgSO4) and concentrated under reduced pressure. The crude product (251 mg) was chromatographed (silica gel, toluene/acetone 3/1) to afford the title compound as a isomeric mixture of syn and anti 20-oximes, both containing a 3-hydroxyimino group in the syn configuration.

Provenance & Evidence