[CH2:1]([OH:4])[C:2]#[CH:3].Cl.Cl[CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:4][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:2]#[CH:3]Propargyl alcohol (1.40 g, 25 mmol) in toluene (30 ml) was treated with 1-(2-chloroethyl)pyrrolidine hydrochloride (8.55 g, 50 mmol), 10 N aqueous sodium hydroxide solution (30 ml) and tetrabutylammonium bromide (150 mg, 1.2 mmol) and heated at 90° C. for 18 h. The layers were separated and the organic layer was dried over sodium sulphate and concentrated under reduced pressure to give a gum. The gum was distilled on a kugelrohr at 160° C. at 22 mbar to give two fractions. Fraction 1 (4.01 g, 25 mmol), the higher boiling, was found to be a mixture of the desired compound I-(2-prop-2-ynoxyethyl)pyrrolidine with some toluene and 2-pyrrolidine-lylethanol. Fraction 2 (2.7 g) was found to be mainly the 2-pyrrolidine-lylethanol and toluene and a trace of the desired compound I-(2-prop-2-ynoxyethyl)pyrrolidine. A portion of fraction 1 (1 g) was repurified by chromatography on silica in a gradient of 2-12% methanol in dichloromethane on a 100 g silica column collecting column volumes. 1-(2-Prop-2-ynoxyethyl)pyrrolidine was isolated as a yellow oil (0.419 g).
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