HCID 52919353, compound → HCID 58250163, compound

Participants

Reaction Steps

To a stirred solution of tert-butyldiphenyl(12-(phenylsulfonyl)dodecyloxy)silane (0.381 g, 0.675 mmol) in THF (2 mL) was added n-BuLi (2.5 M solution in hexanes, 0.297 mL, 0.742 mmol) at −78° C. under Argon. After stirring the resulting solution for 30 min, the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was quenched with saturated aqueous NH4Cl (2 mL) at −10° C. and the aqueous phase was extracted with DCM (3×15 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude was purified by silica gel column chromatography using 5% ethyl acetate/hexane to afford the title product as a clear thick oil (0.16 g, 85%). 1H NMR (CDCl3): δ7.89-7.39 (m, 15H), 5.37 (m, 8H), 3.64 (t, 2H, J=6.5 Hz), 2.78 (m, 7H), 2.08 (m, 4H), 1.82 (m, 2H), 1.37-1.20 (m, 30H), 1.04 (s, 9H), 1.04 (t, 3H, J=6.7 Hz). m/z (ESI) 837.74 (M++1).

Provenance & Evidence