
2H-1,2,3-TRIAZOLE-2-ETHANOL synthesis
- Product Name:2H-1,2,3-TRIAZOLE-2-ETHANOL
- CAS Number:146984-27-2
- Molecular formula:C4H7N3O
- Molecular Weight:113.12
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