(1H-BENZO[D][1,2,3]TRIAZOL-5-YL)METHANOL synthesis

7synthesis methods

Product Name:(1H-BENZO[D][1,2,3]TRIAZOL-5-YL)METHANOL
CAS Number:106429-67-8
Molecular formula:C7H7N3O
Molecular Weight:149.15

METHYL 1,2,3-BENZOTRIAZOLE-5-CARBOXYLATE

113053-50-2
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(1H-BENZO[D][1,2,3]TRIAZOL-5-YL)METHANOL

106429-67-8
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Yield:106429-67-8 81%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 20; for 4 h;

Steps:

LiAlH₄ (0.316 g, 7.90 mmol) and THF (15 mL). Methyl lH-benzo[d][l,2,3]triazole- 5-carboxylate (1.0 g, 5.64 mmol) was then added portion-wise over lOmin at room temperature and reaction allowed to stir for 4 hours at which time the reaction was quenched with EtOAc (5 mL), and the mixture poured into ice-water. The mixture was acidified to pH = 3 with 10% H₂SO₄ and extracted 4X with EtOAc. The combined organics were washed with brine, dried (MgSO₄) and the solvent removed. The resulting brown solid was boiled in Et₂O and the solids filtered and dried to give the title compound as a light brown solid (678 mg, 81 %). ¹H NMR (400 MHz, CD₃OD) δ 7.85 (m, 2H), 7.47 (d, J= 8.4 Hz, IH), 4.79 (s, 2H); MS ESI 150.0 [M + H]⁺, calcd for [C₇H₇N₃O + H]⁺ 150.16.