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

HRID 1189140Notes

Reaction equation

HRID 1189140 reaction equation
[Li]CCCC.[CH3:6][Si:7]([CH3:12])([CH3:11])[C:8]#[C:9][CH3:10].Cl[CH2:14][C:15]1[N:19]([CH3:20])[C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]=1>C1COCC1>[CH3:20][N:19]1[C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]=[C:15]1[CH2:14][CH2:10][C:9]#[C:8][Si:7]([CH3:12])([CH3:11])[CH3:6]

Participants

5

Reactant 3

HCID 803631-(Trimethylsilyl)prop-1-yneHCID 2480442-(Chloromethyl)-1-methylbenzimidazoleHCID 178418339Butyllithium

Product 1

HCID 66597967HCID 66597967, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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 (8 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%).

Workup

  1. customwas quenched with water
  2. extractionThe aqueous phase was extracted with DCM
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-de0cbb9a9b394d43ba1f83af9de35e3d
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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