Tetrabutylammonium Fluoride → HCID 58366210, compound

Participants

Reaction Steps

2-(5-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)-2H-tetrazol-2-yl)-pyridine (4.4 mg, 0.009 mmol) was dissolved in THF (122 μL), treated with Bu4NF (1 M in THF, 0.013 mL, 0.013 mmol) and stirred at room temperature for 2 h under Ar. The reaction mixture was diluted with EtOAc, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude alcohol that was purified by flash chromatography (SiO2, 0.5×4 cm, 20-50% EtOAc-hexanes) to afford 7-phenyl-1-(2-(pyridin-2-yl)-2H-tetrazol-5-yl)-heptan-1-ol (2.7 mg, 79%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 8.69 (dd, 1H, J=1.1, 4.7 Hz), 8.18 (d, 1H, J=8.1 Hz), 8.00 (m, 1H), 7.50 (ddd, 1H, J=0.7, 4.8, 7.4 Hz), 7.26 (m, 2H), 7.16 (m, 3H), 5.16 (m, 1H), 2.59 (t, 2H, J=7.7 Hz), 2.48 (d, 1H(—OH), J=6.1 Hz), 2.07 (m, 2H), 1.61 (m, 2H), 1.52 (m, 2H), 1.40 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 169.5, 149.6, 148.8, 142.9, 139.6, 128.5, 128.4, 125.7, 125.3, 115.3, 67.0, 36.7, 36.1, 31.5, 29.3 (2C), 25.2; HRMS-ESI-TOF m/z 338.1966 ([M+H]+, C19H23N5O requires 338.1975).

Provenance & Evidence