Water → HCID 21631643, compound

Participants

Reaction Steps

In a flame-dried round-bottom flask, tetrakis(triphenylphosphine) palladium (59 mg, 0.051 mmol) was added to a degassed solution of compound 58 (400 mg, 1.02 mmol) in DME (5 mL). Phenylboronic acid (186 mg, 1.53 mmol), water (2.5 mL), and Na2CO3 (324 mg, 3.06 mmol) were successively added, degassing and purging with nitrogen between each addition. The mixture was refluxed under nitrogen atmosphere for 3 h and partitioned between Et2O and water. The organic layer was dried over MgSO4 and concentrated in vacuum. The title compound 59 (398 mg, 100% yield) was obtained as a brown oil. 1H NMR: (CDCl3) δ(ppm): 7.51-7.31 (m, 6H), 1.54 (s, 18H). m/z: 413.5 (M+Na+). This procedure is essentially as described in Brugier et al., Tetrahedron, 56: 2985-2993 (2000), which is incorporated by reference in its entirety.

Provenance & Evidence