Tris(1,1-dimethylethyl)phosphine → HCID 59807036, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Pd2(dba)3 (0.124 g, 0.136 mmol) and PtBu3 (1.65 mL, 0.544 mmol, 10% wt in hexane) in anhydrous THF (5 mL) was treated with a solution of compound 3 (1.0 g, 2.722 mmol) in THF (15 mL) followed by LiHMDS (5.44 mL, 5.445 mmol, 1 M solution in THF) at room temperature. The resulting dark brown mixture was heated to 100° C. and stirred for 3 hours in a sealed tube. The reaction mixture was cooled to room temperature and treated with TBAF (5 mL, 1 M solution in THF) and stirred for 20 min. The reaction was diluted with water (25 mL) and product was extracted into ether (3×30 mL) and the combined organic fractions were dried (Na2SO4) and concentrated to give a dark brown residue. The crude product was purified by column chromatography (2 N NH3 in methanol:CH2Cl2, 3:97) to obtain compound 4 (0.68 g, 82%) as a foam. ESI-MS (m/z, %): 304 (MH+, 16), 248 (100), 134 (25).

Provenance & Evidence