Imidazole → tert-Butyl-diphenyl-[5-(tetrahydro-pyran-2-yloxy)-pent-2-ynyloxy]-silane

Participants

Reaction Steps

A solution of compound 3 and imidazole in CH2Cl2 was treated with TBDPSCl dropwise at 0° C. for 2 h. The reaction mixture was diluted with CH2Cl2 (300 mL) and washed with water (200 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified with 10% EtOAc in hexanes by silica gel column chromatography to give 18.0 g of compound 4 (42.6 mmol, 96% yield): 1H NMR (CDCl3) δ 7.80˜7.64 (m, 4H), 7.49˜7.34 (m, 6H), 4.63 (t, J=3.6 Hz, 1H), 4.31 (t, J=1.9 Hz, 2H), 3.93˜3.83 (m, 1H), 3.77 (dt, J=9.7, 7.1 Hz, 1H), 3.55˜3.44 (m, 2H), 2.48 (tt, J=7.1, 2.1 Hz, 2H), 1.89˜1.46 (m, 6H), 1.06 (s, 9H).

Provenance & Evidence