Tris(1,1-dimethylethyl)phosphine → HCID 59807117, compound

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (0.077 g, 0.084 mmol) in dry THF (3 mL) was treated with PtBu3 (1.04 mL, 0.338 mmol, 10% wt in hexanes) at room temperature. The mixture was treated with compound 3 (0.5 g, 1.693 mmol) in dry THF (7 mL) followed by LiHMDS (3.4 mL, 3.387 mmol, 1 M solution in THF) and the resulting mixture was stirred at 100° C. (sealed tube) for 2 h. The reaction was brought to room temperature, quenched with 1 N HCl solution (10 mL) and stirred for 10 min. The solution was made basic with 1 N NaOH solution (50 mL) and product was extracted into ethyl acetate (2×25 mL). The combined ethyl acetate layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography on silica gel (2 M NH3 in MeOH:CH2Cl2, 2:98 to 5:95) to obtain compound 4 (0.14 g, 36%) as a foam that was used directly in the next step.

Provenance & Evidence