Propargyl alcohol → 3-(Furan-3-yl)prop-2-yn-1-ol

To a mixture of 3-bromofuran (10 g, 0.068 mol) and propargyl alcohol (4.3 ml, 0.074 mol) in 200 ml of TEA was added under argon, CuI (0.26 g, 1.4 mmol) and [(C6H5)3P]2PdCl2 (1.05 g, 1.4 mmol) and the mixture was stirred at 0° C. for 2 hours and at room temperature for 72 hours. The reaction mixture was cooled, decanted, and the solid was washed with TEA. The combined TEA solution was concentrated in vacuo and the residue was distilled (Kugelrohr distillation) to afford 1.48 g (17.8%) of 3-(3-furyl)-2-propynyl alcohol.

1. additionwas added under argon
2. temperatureThe reaction mixture was cooled
3. customdecanted
4. washthe solid was washed with TEA
5. concentrationThe combined TEA solution was concentrated in vacuo
6. distillationthe residue was distilled
7. distillation(Kugelrohr distillation)

ORD record

ord-4811e0e5185c4edaa91058492b7ebe77

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05554620