Dicyclohexylcarbodiimide → 3-Benzylpyrrolylmethyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate

Participants

Reaction Steps

To a stirred solution of 3-benzylpyrrolylmethyl alcohol (1.8 mmol), 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylic acid (2.0 mmol) and 4-dimethylaminopyridine (0.65 mmol) in 20 ml of methylene chloride and 2 ml of DMF is added N,N'-dicyclohexylcarbodiimide (2 mmol). The reaction mixture is stirred, under nitrogen, for about two hours and then filtered and extracted with water. The aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a rotary chromatograph eluting with ether/hexane to yield 3-benzylpyrrolylmethyl 3-(n-pentyloxy)-2,2-dimethylcyclopropanecarboxylate.

Provenance & Evidence