4-Fluorophenol → HCID 23512174, compound

Participants

Reaction Steps

To a solution of 2-(N-benzyl-N-tert-butoxycarbonylamino)ethanol (6.85 g, 27.3 mmol), 4-fluorophenol (3.07 g, 27.3 mmol) and PPh3 (7.83 g, 30.0 mmol) in THF (100 mL) was added DIAD (6.00 mL, 30.0 mmol) at room temperature. After being stirred for 3 hr, the reaction mixture was concentrated. Chromatography of the residue with hexane-EtOAc (8:1, v/v) as eluent gave 1-[2-(N-benzyl-N-tert-butoxycarbonylamino)ethoxy]-4-fluorobenzene (8.19 g, 64%) as a yellow oil. 1H-NMR (CDCl3) δ1.42-1.50 (m, 9H), 3.41-3.67 (m, 2H), 3.92-4.11 (m, 2H), 4.51-4.63 (m, 2H), 6.73-6.85 (m, 2H), 6.89-6.98 (m, 2H), 7.24 (m 5); FAB-MS m/z 346 (M++1).

Provenance & Evidence