7-Hydroxynaphthalene-2-sulfonamide → 7-(2-(tert-Butyldimethylsilyloxy)ethoxy)naphthalene-2-sulfonamide

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 17, 7-hydroxynaphthalene-2-sulfonamide (40 mg, 0.18 mmol) and (2-bromoethoxy)(tert-butyl)dimethylsilane (43 mg, 0.18 mmol) were converted to the title compound (33 mg, 48%) after purification using flash column chromatography (gradient from 0% to 2% MeOH/CH2Cl2). 1H NMR (CDCl3) δ 8.31 (s, 1H), 7.84-7.82 (m, 1H), 7.77-7.73 (m, 2H), 7.26 (dd, J=8.9, 2.5 Hz, 1H), 7.19 (d, J=2.2 Hz, 1H), 4.13 (t, J=4.9 Hz, 2H), 4.02 (t, J=4.9 Hz, 2H), 0.90 (s, 9H), 0.10 (s, 6H); MS(ESI−) m/z 380.4 (M−H)−.

Provenance & Evidence