2H-1,2,3-TRIAZOLE-2-ETHANOL synthesis

Yield:865350-58-9 70%

Reaction Conditions:

with sodium hydride in DMF (N,N-dimethyl-formamide) at -50 - 20;

Steps:

5.i

207 mg (8.21 mmol) 95% Sodium hydride were given at -50° C. to a solution of 1.00 g (5.47 mmol) 1-allyloxy-4-chloromethyl-benzene and 619 mg (5.47 mmol) 2-(2H-[1,2,3]-triazol-2-yl)-ethanol in 10.0 ml DMF. The mixture was allowed to warm slowly to r.t., stirred overnight and 6 ml water added. The formed oil was collected with 10 ml dichloromethane, the aqueous phase extracted with 10 ml dichloromethane and the combined organic phases dried over Na₂SO₄. Solvents were removed in vacuum and the residue purified by chromatography on silica gel (ethyl acetate/heptane 1:1) to yield 992 mg (70%) pale yellow oil. MS: M=282.3 (ESI+, M+Na⁺). ¹H-NMR(400 MHz, D₆-DMSO): δ=3.86(t, 2H, C₂-CH₂-triazole), 4.35(s, 2H, OCH₂Ph), 4.54(d, 2H, OCH₂-vinyl), 4.59(t, 2H, CH₂-triazole), 5.24(d, 1H, =CH₂), 5.37(d, 1H, =CH₂), 6.04(m, 1H, C=CH₂), 6.88(d, 2H, 2'-/6'-H), 7.12(d, 2H, 3'-/5'-H), 7.77(s, 2H, triazole).

References:

US2005/209290,2005,A1 Location in patent:Page/Page column 12