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

HRID 1046783Notes

Reaction equation

HRID 1046783 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%

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 (17g, 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-fca0d3951dc74511af25180362fa3ba4
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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