Water → HCID 20217094, compound

Participants

Reaction Steps

To a slurry of lithium aluminum hydride 1.0892 g (27.3 mmol) in 200 ml of ether under a nitrogen atmosphere, a solution of 2 g (6.82 mmol) of 1-hydroxy-3-(3-phenoxyphenyl-1-(2-pyrrolyl)propane, dissolved in ether was added over a period of 5 min. The mixture was stirred at room temperature for 19 hours and then refluxed for an additional 75 min. The mixture was cooled in an ice bath and 1 ml of water was added followed by 1 ml of 15% w/w NaOH solution followed by 3 ml of water. The mixture was stirred for 30 min. The solids were filtered off and the filtrate was evaporated to dryness yielding 2 g of amber oil. After three chromatographic runs (on silica gel for dry column chromatography), in which the eluants were mixtures of ethyl acetate and hexane, 1.26 g of pure product 10 was obtained as an oil.

Provenance & Evidence