Boron trifluoride etherate → HCID 18791738, compound

Temperature

5 °C

1-Bromoethylbenzene (2.2 ml, 17 mmol) in anhydrous tetrahydrofuran (30 ml) was added dropwise to a stirred solution of a cooled (-5° C.) mixture of zinc (2.7 g, 41.5 mmol) in anhydrous tetrahydrofuran (5 ml). The mixture was allowed to warm to 5° C. and stirred for 2 hours. This mixture was added to a stirred mixture of copper(1)cyanide (1.25 g, 14 mmol) and lithium chloride (1.25 g, 30 mmol) in tetrahydrofuran (15 ml) at -78° C., under nitrogen. The mixture was allowed to warm to -20° C. for 5 minutes then re-cooled to -78° C. This mixture was treated with boron trifluoride diethyl etherate (3.5 ml, 28 mmol) followed by a solution of the foregoing aldehyde (1.7 g, 14 mmol) in tetrahydrofuran (10 ml). The mixture was allowed to warm to room temperature whilst stirring overnight. The solvent was evaporated and the residue partitioned between water and dichloromethane. The organic layer was dried (sodium sulphate), the solvent evaporated and the residue purified by column chromatography on silica using dichloromethane/methanol (gradient). The title compound was obtained as a mixture of diastereomers (350 mg, 12%). MS, ES+, m/z=228 for (M+H)+.

1. temperaturea cooled
2. temperatureto warm to -20° C. for 5 minutes
3. temperaturethen re-cooled to -78° C
4. temperatureto warm to room temperature
5. stirringwhilst stirring overnight
6. customThe solvent was evaporated
7. customthe residue partitioned between water and dichloromethane
8. dry with materialThe organic layer was dried (sodium sulphate)
9. customthe solvent evaporated
10. customthe residue purified by column chromatography on silica

ORD record

ord-ec0c041db11f49e09fdbe95b17efd641

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06054469