Tributyltin Chloride → 2-Methoxy-5-(tributylstannyl)-1,3-thiazole

HRID 2069093Notes

Reaction equation

HRID 2069093 reaction equation
Br[C:2]1[S:6][C:5]([O:7][CH3:8])=[N:4][CH:3]=1.C([Li])CCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].C(=O)(O)[O-].[Na+]>C(OCC)C>[CH3:8][O:7][C:5]1[S:6][C:2]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:3][N:4]=1

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 164271345-Bromo-2-methoxy-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 164271192-Methoxy-5-(tributylstannyl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A diethyl ether (1.8 mL) solution of 5-bromo-2-methoxythiazole (200 mg) was cooled to −78° C. followed by the dropwise addition of normal butyllithium (1.6 M, 0.7 mL; KANTO). The resulting mixture was stirred as it was for 1 hour, followed by the addition of tri-n-butyltin chloride (0.35 mL; TCI), and the resulting mixture was slowly raised to room temperature and then stirred for 2 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture solution, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried and the solvent was evaporated under reduced pressure to give the'title compound.

Workup

  1. stirringstirred for 2 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. customto give the'title compound

Sources & evidence

ORD record
ord-17672767238542d59f3b683193cec61a
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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