Tetrahydrofuran → HCID 11207080, compound

Temperature

-78 °C

A 70 ml THF solution of the Part G dibromide (5.48 g, 13.3 mmol) under argon atmosphere was cooled to -78° C. n-Butyllithium (10.6 ml of a 2.5M solution in hexane, 26.5 mmol) was added to the dibromide solution over 10 minutes. The reaction was stirred at -78° C. for 1 hour and then quenched at -78° C. with saturated aqueous NH4Cl solution. After the reaction was warmed to room temperature, it was diluted with 60 ml of H2O, and the aqueous layer was extracted 2 times with ether. All of the organic layers were combined and dried over MgSO4. Filtration and solvent removal gave 3.8 g of title benzyloxyacetylene in the form of a yellow solid. The title benzyloxyacetylene was purified by flash chromatography eluting with 3% ether/hexane. Title acetylene was obtained in 85% yield (2.76 g) as a white solid.

1. customquenched at -78° C. with saturated aqueous NH4Cl solution
2. temperatureAfter the reaction was warmed to room temperature
3. additionit was diluted with 60 ml of H2O
4. extractionthe aqueous layer was extracted 2 times with ether
5. dry with materialdried over MgSO4
6. filtrationFiltration and solvent removal

ORD record

ord-08be79e71e474f86a3ccb3cc0643fc6c

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05091378