Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 422337Generated: October 29, 2026

1-(Trimethylsilyl)prop-1-yne → HCID 66597967, compound

https://huagongshe.com/reaction/422337

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-(Trimethylsilyl)prop-1-yneHCID 80363—
Reactant2-(Chloromethyl)-1-methylbenzimidazoleHCID 248044—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
ProductHCID 66597967HCID 6659796723%

Reaction Conditions

Temperature-78 °C

Reaction Steps

n-BuLi (1.35 mL, 3.39 mmol, 2.5 M) was added to a solution of trimethyl-prop-1-ynyl-silane (0.55 mL, 3.69 mmol) in THF (1 mL) at −78° C. After 2 hours, a solution of 2-chloromethyl-1-methyl-1H-benzoimidazole (556 mg, 3.08 mmol) in THF (5 mL) was added to the reaction mixture at −78° C. then the reaction mixture was stirred for 30 min at −78° C. and 1 hour at room temperature and was quenched with water. The aqueous phase was extracted with DCM. The organic phase was washed with water, dried over MgSO4, filtered and evaporated to yield 1-methyl-2-(4-trimethylsilanyl-but-3-ynyl)-1H-benzoimidazole (178 mg, 0.69 mmol, 23%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08101637B2
Source datasetuspto-grants-2012_01
ORD IDord-cb0f7de90ef74d91b13f79990360995c
Source noteuspto-grants-2012_01