Propargyl alcohol → HCID 87814959, compound

Temperature

90 °C

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).

1. customThe layers were separated
2. dry with materialthe organic layer was dried over sodium sulphate
3. concentrationconcentrated under reduced pressure
4. customto give a gum
5. distillationThe gum was distilled on a kugelrohr at 160° C. at 22 mbar
6. customto give two fractions

ORD record

ord-40c58c20b7854bdba2e16d2489a5f81d

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290511B2