Potassium Carbonate → HCID 89681748, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-ethyl 2-(5-bromo-3-methyl-1-(methylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (0.47 g, 0.99 mmol) in toluene/EtOH (6 mL/2.5 mL) was treated with trimethylboroxine (0.42 mL, 3 mmol), PdCl2dppf (0.036 g, 0.05 mmol) and K2CO3 (2M, 1.5 mL, 3 mmol). The vessel was sealed and sparged with Ar for 20 minutes prior to heating in a microwave reactor at 125° C. for 90 minutes. The reaction mixture was loaded directly onto silica gel and purified via Yamazen column chromatography to afford (S)-ethyl 2-tert-butoxy-2-(3,5-dimethyl-1-(methylsulfonyloxy)naphthalen-2-yl)acetate that was approximately an 85:15 mixture with an inseparable, uncharacterized side product. 1H-NMR: 400 MHz, (CDCl3) δ: 8.09 (br d, J=8.4 Hz, 1H); 7.77 (s, 1H); 7.44 (dd, J=8.4, 7.2 Hz, 1H); 7.35 (d, J=7.2 Hz, 1H); 5.77 (s, 1H); 4.27-4.09 (m, 2H); 3.43 (s, 3H); 2.68 (s, 3H); 2.63 (s, 3H); 1.24 (s, 9H); 1.20 (t, J=7.2 Hz, 3H).

Provenance & Evidence