Trimethyltin chloride → HCID 90403110, compound

HRID 1049266Notes

Reaction equation

HRID 1049266 reaction equation
[CH:1]([C:4]1[N:5]([CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:6]=[CH:7][N:8]=1)([CH3:3])[CH3:2].[Li]CCCC.[CH3:20][Sn:21](Cl)([CH3:23])[CH3:22]>C1COCC1.CCOC(C)=O>[CH:1]([C:4]1[N:5]([CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[C:6]([Sn:21]([CH3:23])([CH3:22])[CH3:20])=[CH:7][N:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14016Trimethyltin chlorideHCID 90402630HCID 90402630, compoundHCID 178418339Butyllithium

Product 1

HCID 90403110HCID 90403110, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A −78° C. solution of 2-isopropyl-1-((2-methoxyethoxy)methyl)-1H-imidazole (1.50 g, 7.57 mmol) in THF (30 mL) was treated drop-wise with n-BuLi (2.5N, 4.24 mL, 10.59 mmol), stirred for 10 min, then warmed to 0° C. for 45 min. The solution was re-cooled to −78° C., treated drop-wise, with trimethyltin chloride (1.0 N, 7.19 mL, 7.19 mmol), over 5 min, warmed to RT and stirred overnight. The mixture was diluted with EtOAc, washed with brine, dried over Na2SO4 and concentrated to dryness to afford 2-isopropyl-1-((2-methoxyethoxy)methyl)-5-(trimethylstannyl)-1H-imidazole (2.45 g, 90%). MS (ESI) m/z: 363.1 (M+H+).

Workup

  1. temperatureThe solution was re-cooled to −78° C.
  2. additiontreated drop-wise
  3. temperaturewarmed to RT
  4. stirringstirred overnight
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fafe5e21a93b407ab7c9fd51643da9bb
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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