Trimethyltin chloride → 1-Methyl-5-(trimethylstannyl)-1H-1,2,3-triazole

To a stirred solution of 1-methyl-1H-1,2,3-triazole (0.5 g, 6.0 mmol) in anhydrous tetrahydrofuran (50 mL) at −78° C. under an atmosphere of nitrogen was added n-butyllithium (2.5M solution in hexanes, 2.6 mL, 6.6 mmol) dropwise over ten minutes. On complete addition the reaction was allowed to warm to −30° C. and stirred for 2 h. A solution of chlorotrimethylstannane (1.3 g, 6.6 mmol) in tetrahydrofuran (2 mL) was added dropwise over 10 minutes then the reaction mixture was allowed to warm to room temperature over 2 h. The reaction was quenched by the addition of saturated ammonium chloride solution (5 mL) then diluted with water (20 mL). The solvent was evaporated in vacuo and the aqueous phase extracted with ethyl acetate (2×30 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated to afford a pale yellow oil (1.4 g, 90%). 1H NMR (DMSO-D6, 400 MHz): 7.61 (s, 1H), 4.04 (s, 3H), 0.40 (s, 9H).

1. additionOn complete addition the reaction
2. temperatureto warm to room temperature over 2 h
3. customThe reaction was quenched by the addition of saturated ammonium chloride solution (5 mL)
4. additionthen diluted with water (20 mL)
5. customThe solvent was evaporated in vacuo
6. extractionthe aqueous phase extracted with ethyl acetate (2×30 mL)
7. dry with materialThe combined organic layer was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD-Eintrag

ord-60807e03c07a4d589bf203128d03b5e4

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09216980B2