Phosphate → HCID 54552717, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 105 (900 mg, 3 mmol) in THF (20 mL) was treated with Bu4NF (1 M in THF, 3 mL, 3 mmol, 1 equiv) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and at 25° C. for 2 h. Phosphate buffer (100 mL, pH 7) was added and the mixture was extracted with EtOAc-hexane (2:1, 3×30 mL). The combined organic phase was dried (Na2SO4) and the solvent removed under vacuum. Chromatography (SiO2, 4×25 cm, 30% EtOAc-hexane containing 2% Et3N) afforded 106 (445 mg, 557 mg theoretical, 80%) as a colorless oil as a mixture of E- and Z-olefin isomers (50:50). Careful rechromatography of this material (SiO2, 4×25 cm, 10-30% EtOAc-hexane containing 2% Et3N gradient elution) enabled the partial separation of the two isomers.

Provenance & Evidence