Trimethyltin chloride → HCID 59168358, compound

HRID 2195054Notes

Reaction equation

HRID 2195054 reaction equation
[CH3:1][Sn:2](Cl)([CH3:4])[CH3:3].Cl[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH:13]([CH3:15])[CH3:14])[CH:8]=1>COCCOC>[CH:13]([C:9]1[CH:8]=[C:7]([Sn:2]([CH3:4])([CH3:3])[CH3:1])[CH:12]=[CH:11][N:10]=1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 14016Trimethyltin chlorideHCID 134980014-Chloro-2-(propan-2-yl)pyridine

Product 1

HCID 59168358HCID 59168358, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a cold suspension (0° C.) of Na (25% in toluene, 10 g, 104 mmol) in DME (100 mL) add a solution of trimethyltin chloride (9.4 g, 47.4 mmol) in DME (20 mL) dropwise. Stir the mixture at 0° C. for 3 h followed by addition of the solution of cold (0° C.) 4-chloro-2-isopropyl-pyridine (Comins & Mantlo (1985) J. Org. Chem. 50:4410-4411) (4.9 g, 31.6 mmol) in DME (20 mL). Stir the mixture at 0° C. for 2 h and warm to room temperature. Filter, concentrate the filtrate, and dilute the residue with ether. Filter and concentrate the filtrate. Distil the residue (bp 75-80° C. at 1 mm Hg) to afford the title compound as a light oil.

Workup

  1. stirringStir the mixture at 0° C. for 2 h
  2. temperaturewarm to room temperature
  3. filtrationFilter
  4. concentrationconcentrate the filtrate
  5. additiondilute the residue with ether
  6. filtrationFilter
  7. concentrationconcentrate the filtrate
  8. customDistil the residue (bp 75-80° C. at 1 mm Hg)

Sources & evidence

ORD record
ord-295b0e9ca61f412c8c36e185889cf964
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

Loading…