Tetrabutylammonium Fluoride → HCID 19380935, compound

Participants

Reaction Steps

To a stirred solution of the silyl ether 3 (27 g, 81 mmol) in THF (270 mi) at ambient temperature was added a premixed solution of n-Bu4NF (1M in THF: 244 mL, 0.24 mol) and AcOH (14 mL, 0.24 mmol) (1:1). After 20 hours the reaction mixture was diluted with ether and then washed with H2O (2 times) and brine, dried (MgSO4), and concentrated to give the alcohol 4 (19 g) as a yellow crystalline solid. TLC Rf=0.35 (60% ethyl acetate/hexanes); 1H NMR (CDCl3) δ 8.42 (m, 1H), 7.55 (d, J=7 Hz, 1H), 7.36 (t, J=7 Hz, 1H), 7.29 (t, J=7 Hz, 1H), 7.27 (7d, J=7 Hz, 1H), 7.22 (s, 1H), 3.76 (t, J= 7 Hz, 2H), 2.82 (t, J=7 Hz, 2H) 2.61 (s, 3H), 2.00 (m, 2H).

Provenance & Evidence