Reaction #1520372
Related Literature (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US09266896B2
Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: tert-Butyl-(4-fluorofuran-2-ylmethoxy)dimethylsilane (prepared according to Heffernan et al, US2008 0058395, 6.75 g) was dissolved in anhydrous THF (100 mL), under an atmosphere of nitrogen and cooled to −78° C. n-Butyllithium (2.5M in hexanes, 11.74 mL) was added and the mixture was stirred at −78° C. for 10 minutes. Chlorotrimethylsilane (3.19 g) was added and the mixture was stirred at −78° C. for 40 minutes. Further n-butyllithium (2.5M in hexanes, 11.74 mL) was added and the mixture was stirred at −78° C. for 40 minutes, before triisopropyl borate (11.04 g) was added. The resultant mixture was stirred at −78° C. for 5 minutes then allowed to warm to room temperature. 1M aqueous hydrochloric acid (100 mL) and diethyl ether (50 mL) were added and the mixture was stirred vigorously for 5 minutes. The layers were separated and the organic layer was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-20% to give 2-(tert-butyldimethylsilanyloxymethyl)-4-fluoro-5-trimethylsilanylfuran-3-yl-boronic acid (6.01 g) as a brown oil which was used without further characterisation. was added the mixture was stirred at −78° C. for 40 minutes was added to warm to room temperature the mixture was stirred vigorously for 5 minutes The layers were separated the organic layer was dried (MgSO4) filtered The filtrate was concentrated in vacuo the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-20%
Source ID: ord-2cdc9f18c127494d8d901a1e8bc7014f