Methanol → 1-Propyl-1H-1,2,4-triazole-3-methanol

HRID 1383835Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[N:14]=[CH:13][N:12]([CH2:15][CH2:16][CH3:17])[N:11]=1)(C(C)(C)C)(C)C.CO.[OH-].[Na+]>C(O)C>[CH2:15]([N:12]1[CH:13]=[N:14][C:10]([CH2:9][OH:8])=[N:11]1)[CH2:16][CH3:17]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 3-(tert-butyldimethylsilanyloxymethyl)-1-propyl-1H-1,2,4-triazole (from Example 74, Step a) (2.97 g, 11.6 mmol) in ethanol (13 ml) and methanol (26 ml) was added 4 M aqueous NaOH (4.3 ml, 17.4 mmol) and the mixture was stirred at 45° C. for 2 days. The solvents were removed in vacuo and the residue was purified by flash chromatography (silica gel, EtOAc, then 10% MeOH/CH2Cl2) to leave 1.509 g (92%) of the title compound as a white solid: 1H NMR (250 MHz, CDCl3) δ 0.94 (3H, t, J=7.4 Hz), 1.92 (2H, sextet, J=7.4 Hz), 4.10 (2H, t, J=7.1 Hz), 4.76 (2H, s), 8.01 (1H, s).

Workup

customThe solvents were removed in vacuo
customthe residue was purified by flash chromatography (silica gel, EtOAc

Sources & evidence

ORD record: ord-6c678cd5b6724317b4919ae8307be1d1
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255305B1

Reaction notes

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