Nitrogen → HCID 67128437, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 2-(3-bromo-phenyl)-2-methyl-[1,3]dioxolane (3.620 g, 14.89 mmol), 2-di-t-butylphosphino-2′-methylbiphenyl (931 mg, 2.98 mmol), tri-potassiumphosphate monohydrate (11.063 g, 52.12 mmol) and palladium(II)acetate (334 mg, 1.49 mmol) in toluene (74 mL) was treated with ethyl acetoacetate (2.45 mL, 19.36 mmol). The reaction mixture was heated at 90° C. for 2 h followed by 4 h at 100° C. The reaction mixture was cooled to rt, water (100 mL) was added and the mixture was stirred for 30 min at rt. The org. layers was separated and washed twice with 5% aq. NaCl (50 mL), brine (50 mL) dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as an orange oil. TLC: rf (4:1 hept-EA)=0.37. LC-MS-conditions 02: tR=0.96 min, [M+H]+=251.21.

Provenance & Evidence