Water → 4-Methyl-2-(tributylstannyl)-1,3-thiazole

HRID 1514618Notes

Reaction equation

HRID 1514618 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15].O>O1CCCC1>[CH3:6][C:7]1[N:8]=[C:9]([Sn:16]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][CH2:14][CH3:15])[S:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 127484-MethylthiazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 164271304-Methyl-2-(tributylstannyl)-1,3-thiazoleYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of n-butyl lithium (2.71 M hexane solution, 3.9 ml) in tetrahydrofuran (10 ml) was cooled to −78° C. under argon atmosphere, and thereto was added dropwise a solution of 4-methylthiazole (1.0 g) in tetrahydrofuran (10 ml). The mixture was stirred at same temperature for one hour and thereto was added dropwise a solution of tri-n-butyltin chloride (3.6 g) in tetrahydrofuran (10 ml). The mixture was stirred at same temperature for 30 minutes, warmed, and further stirred at room temperature overnight. Thereto was added water, and the mixture was extracted with diethyl ether. The extract was washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by alumina column chromatography (hexane) to give the title compound (1.76 g) as oil. APCI-Mass m/z 386/388 (M+H)

Workup

  1. stirringThe mixture was stirred at same temperature for 30 minutes
  2. temperaturewarmed
  3. stirringfurther stirred at room temperature overnight
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by alumina column chromatography (hexane)

Sources & evidence

ORD record
ord-b76da77d086e4bd1b18f7781511cec3d
Source dataset
uspto-grants-2012_07
Patent number
US08222219B2

Reaction notes

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