Trimethyltin chloride → HCID 22164812, compound

HRID 1032731Notes

Reaction equation

HRID 1032731 reaction equation
Br[C:2]1[S:6][CH2:5][N:4]([CH3:7])[CH:3]=1.C([Li])CCC.[CH3:13][Sn:14](Cl)([CH3:16])[CH3:15]>CCOCC>[CH3:7][N:4]1[CH:3]=[C:2]([Sn:14]([CH3:16])([CH3:15])[CH3:13])[S:6][CH2:5]1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 54179485HCID 54179485, compoundHCID 178418339Butyllithium

Product 1

HCID 22164812HCID 22164812, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4.45 g 5-bromo-3-methylthiazole in 50 ml dry ether was cooled to -° C. and treated dropwise over 10 min. with butyllithium (10.5 ml, 26.25 mmol). The mixture was stirred at -° C. for 15 min., and a solution of 5.20 g trimethyltin chloride in 20 ml ether was added dropwise over 10 min. The reaction mixture was allowed to warm to room temperature, stirred overnight, and then washed with water. The ether layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 6.60 g 3-methyl-5-trimethylstannylthiazole as a light-brown liquid used directly in the next reaction.

Workup

  1. stirringstirred overnight
  2. washwashed with water
  3. dry with materialThe ether layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16da81382dcb49d397307ea03eff5b2f
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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