Water → [4-(Aminomethyl)phenyl]methanol

Participants

Reaction Conditions

Reaction Steps

Azide 5 (1.96 g, 12.0 mmol) and PPh3 (6.50 g, 24.8 mmol, 2.05 eq) were dissolved in THF (25 ml) and heated at 60° C. for 1 hour. Water (4.5 ml, 248 mmol, 20 eq) was added and the reaction was heated overnight. The solvent was evaporated and the residue obtained was purified by flash chromatography (eluent DCM to 4:1 DCM/methanol saturated with NH3) to yield 6 as a white solid (1.44 g, 10.5 mmol, 85%). Rf=0.05 (9:1, DCM/MeOH sat. NH3); νmax=cm−1; 1H NMR (300 MHz, CDCl3) δ=7.35 (d, 3J(H,H)=8.4 Hz, 2H, ArCH α to CH2NH2), 7.30 (d, 3J(H,H)=8.4 Hz, 2H, ArCH α to CH2OH), 4.67 (s, 2H, CH2OH), 3.85 (s, 2H, CH2NH2), 1.68 (bs, 3H, OH, NH2); 13C NMR (75 MHz, CDCl3) δ=142.6 (ArCCH2NH2), 139.6 (ArCCH2OH), 127.3 (ArCH), 127.2 (ArCH), 65.0 (CH2OH), 46.2 (CH2NH2); HRMS (ESI+): m/z calculated for C8H12NO [M+H]+: 138.0913, found 138.0933.

Provenance & Evidence