Ethyl Acetate → HCID 131730736, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of trifluoromethanesulfonic acid 1,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]octa-2,6-dien-3-yl ester (as prepared in the previous step, 1.22 g, 2.24 mmol), Pd(PPh3)4 (259 mg, 0.224 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (540 mg, 2.46 mmol) in 20 mL of 1,4-dioxane was added 2.0 M aqueous Na2CO3 solution (9.0 mL, 18 mmol). The resulting mixture was stirred at 80° C. for 2 h and then cooled to RT. Treated with 100 mL of EtOAc, the mixture was washed with H2O (3×20 mL), brine (20 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1:1 hexane/DCM-DCM) gave 802 mg (73% for two steps) of the title compound as a light brown oil. Mass spectrum (ESI, m/z): Calcd. for C27H45NO3Si2, 488.3 (M+H), found 488.4.

Provenance & Evidence