Sodium borohydride → [4-(Azidomethyl)phenyl]methanol

Participants

Reaction Steps

Azide 4 (2.0 g, 12.4 mmol) was dissolved in MeOH (50 ml) and cooled to 0° C. before NaBH4 was added slowly and the reaction mixture was stirred for 1 hour, after which the solvent was evaporated. The residue obtained was dissolved in ethyl acetate (50 ml) and water (50 ml), the phases were separated and the organic phase was washed with water (100 ml), dried over Na2SO4, and evaporated to yield 5 as a clear oil (1.96 g, 12.0 mmol, 97%). Rf=0.45 (DCM); νmax=cm−1; 1H NMR (300 MHz, CDCl3) δ=7.40 (d, 3J(H,H) 8.2 Hz, 2H, ArCH α to CH2OH), 7.33 (d, 3J(H,H)=8.2 Hz, 2H, ArCH α to CH2N3), 4.71 (s, 2H, CH2OH), 4.34 (s, 2H, CH2N3), 1.80 (bs, 1H, OH); 13C NMR (75 MHz, CDCl3) δ=141.0 (ArCCH2OH), 134.7 (ArCCH2N3), 128.5 (ArCH α to CH2N3), 127.4 (ArCH α to CH2OH), 64.9 (CH2OH), 54.5 (CH2N3).

Provenance & Evidence