Dimethylformamide → [3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester

Participants

Reaction Steps

5-Hydroxy-1H-indole-3-acetic acid ethyl ester (560 mg. 1,8 mmol) was dissolved in 25 mL of THF and 75 mL of DMF and 80 mg (2.0 mmol) of 60% NaH/mineral oil added. After 0.17 hours, 465 mg (2.0 mmol) of (3-bromopropyl)phosphonic acid dimethyl ester was added and stirring maintained for 3.0 hours. The mixture was diluted with water and ethyl acetate, the organic layer separated, washed with water, brine and dried (Na2SO4). The solution was evaporated at reduced pressure and the residue chromatographed on florisil eluting with a gradient, 1% MeOH/methylene chloride→3% MeOH/methylene chloride, to give 590 mg (71% yield) of [3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester.

Provenance & Evidence