Diethyl benzylphosphonate → HCID 58986363, compound

Participants

Reaction Steps

To a −78° C. solution of diethyl benzylphoshonate (91 mg, 0.4 mmol) in THF (5 mL) was added a 2 M solution of LDA and THF (0.2 mL, 0.4 mmol), and the solution was warmed to RT over 20 min. A solution of 1-benzyl-2-isopropyl-5-(tetrahydropyran-2-yloxy)-1H-indole-3-carboxaldehyde (Compound 13, 100 mg, 0.27 mmol) and THF (2 mL) was added, and the solution was stirred for 1 h at ambient temperature. The solution was diluted with EtOAc (50 mL), and washed with brine (10 mL), and dried (Na2SO4), and the solvent was removed under vacuum. Silica gel flash chromatography using 20% EtOAc in hexane gave (E)-1-benzyl-2-isopropyl-3-(2-phenylethen-1-yl)-5-(tetrahydropyran-2-yloxy)-1H-indole (Compound 26) as a colorless oil.

Provenance & Evidence