Sodium Nitrite → HCID 178472910, compound

Reaction equation

[N:1]([O-:3])=O.[Na+].[CH3:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:10][CH:11]=1>O.C(O)(=O)C>[OH:3][N:1]=[C:15]([C:14](=[O:21])[CH2:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH3:5])[CH:7]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Procedure

Sodium nitrite (32 g) in water (60 ml) was added dropwise over 1 hour to a stirred solution of the product from example 13 step (i) (99.4 g) in acetic acid (200 ml) at a rate such that the internal temperature did not rise above 30° C. The solution was allowed to stir a further 1 hour before adding water (500 ml). After stirring for a further 24 h the reaction mixture was extracted with diethyl ether (×4). The combined ether extracts were washed with saturated sodium bicarbonate solution, and finally water before collecting the organic layer and drying over magnesium sulphate. The solution was filtered and the solvent evaporated under reduced pressure to leave the subtitle product.