Trimethyltin chloride → 2-Methyl-5-(trimethylstannyl)thiazole

HRID 2176559Notes

Reaction equation

HRID 2176559 reaction equation
C([Li])CCC.[CH3:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.Cl[Sn:13]([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[CH3:6][C:7]1[S:8][C:9]([Sn:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 771292-MethylthiazoleHCID 178418339Butyllithium

Product 1

HCID 102646602-Methyl-5-(trimethylstannyl)thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Butyllithium (1.6M in THF, 3.5 ml, 5.5 mmol) was added to a stirred solution of 2-methylthiazole (0.45 ml, 5.0 mmol) in THF (15 mL) at −78° C. The reaction mixture was stirred at −78° C. for 40 min. Chlorotrimethylstannane (1M in THF, 5.0 ml, 5.0 mmol) was added. Stirring was continued at −78° C. for 45 min. The reaction mixture was quenched with a saturated aqueous solution of NaHCO3. The aqueous layer was extracted with Et2O. The organic extracts were dried over MgSO4, filtered and concentrated in vacuo. Used in the next step without purification (obtained 1.29 g). MS m/z=264.1. Calc'd for C7H13NSSn: 261.94.

Workup

  1. stirringStirring
  2. waitwas continued at −78° C. for 45 min
  3. customThe reaction mixture was quenched with a saturated aqueous solution of NaHCO3
  4. extractionThe aqueous layer was extracted with Et2O
  5. dry with materialThe organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customUsed in the next step without purification (obtained 1.29 g)

Sources & evidence

ORD record
ord-07cc0373c8754035b070ae1c84d9ce45
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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