Triphenylphosphine → HCID 178472882, compound

Participants

Reaction Steps

Ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(hydroxyimino)acetate (0.91 g), triphenylphosphine (0.58 g) and trans-4-chlorocyclohexanol (0.54 g) were dissolved together in anhydrous benzene (20 ml). Diethyl azodicarboxylate (0 35 ml) was added and the solution heated at reflux for 16 h with exclusion of moisture. Evaporation of solvent followed by chromatography afforded the title compound as a near colourless gum (225 mg, 20%); νmax (KBr) 1737, 1595 (w), 1529, 1491 and 1446 cm-1 ; δHH (CDCl3) 1.39 (3H, t, J 7 Hz), 1.69, 1.96 and 2.06 (8H, 3m), 4.04 (1H, qt, J 6 Hz), 4.39(2H, q, J 7Hz), 4.44 (1H, qt, J 3 Hz), 6.49 (1H, s), 6.97 (1H, brs, D2O exch), and 7.32 (15H, s). [Mass spectrum: +ve ion (thioglycerol) MH+ (574), MNa+ (596)].

Provenance & Evidence