Triphenylphosphine → HCID 14033175, compound

Participants

Reaction Steps

To a mixture of 2,4-dihydroxy-3-propylacetophenone, 40 g, diethyl diazodicarboxylate, 51 g, and cyclohexen-2-ol, 20 g, in tetrahydrofuran, 1.5 L, cooled at 0° C., was added slowly a solution of triphenylphosphine, 80 g, in THF, 0.5 L. The mixture was stirred at room temperature for 18 hours. The volatiles were removed in vacuo. The residue was dissolved in a minimum amount of CH2Cl2 and placed on a silica gel column. Elution with 1% EtOAc/hexane yielded 20 g of the title compound as an oil. NMR (ppm) (CDCl3): 12.75 (1H, s, phenolic OH), 7.60 (1H, d, J-9 Hz, H ortho to acetyl), 6.53 (1H, d, J-9 Hz, H meta to acetyl), 5.90 (2H, m, olefinic proton), 4.87 (1H, m, CHOAc), 2.60 (3H, s, CH3).

Provenance & Evidence