Water → 2-(Tributylstannyl)-1,3-thiazole

HRID 2061112Notes

Reaction equation

HRID 2061112 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Li]CCCC.CCCCCC.[Sn:18](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22].O>CCOCC>[CH2:27]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 764302-BromothiazoleHCID 178418244HCID 178418244, compound

Product 1

HCID 27632592-(Tributylstannyl)-1,3-thiazoleYield 90.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 2-bromothiazole (4.6 mL, 50 mmol) and anhydrous ether (50 mL), there was added an n-BuLi hexane solution (22 mL, 55 mmol) dropwise at −70° C. under nitrogen atmosphere, and the mixture was stirred for 30 minutes. A solution of n-Bu3SnCl (14 mL, 50 mmol) in ether (20 mL) was then added at −70° C., and after stirring for 4 hours, the mixture was raised to room temperature and stirred for another hour. After adding water (50 mL), the organic layer was extracted three times with ether (50 mL), and the solvent was distilled away. It was then purified by silica gel chromatography (hexane:ethyl acetate=20:1) to yield the title compound (17 g, 90%).

Workup

  1. stirringafter stirring for 4 hours
  2. stirringstirred for another hour
  3. extractionthe organic layer was extracted three times with ether (50 mL)
  4. distillationthe solvent was distilled away
  5. customIt was then purified by silica gel chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-5457d8af56d84012bf2fab047b76b919
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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