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

HRID 581909Notes

Reaction equation

HRID 581909 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.CCCCCC.[Sn:17](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21]>C1COCC1>[CH2:26]([Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 8058HexaneHCID 9256ThiazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 27632592-(Tributylstannyl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of thiazole (0.71 ml, 10 mmol) in dry THF (20 ml) was added dropwise 1.6 M-BuLi in hexane (6.9 ml, 11 mmol) under argon at -78° C. The reaction mixture was stirred at -78° C. for 0.5 hr and Bu3SnCl (3.1 ml, 11 mmol) was added dropwise. After stirring for 1 hr at -78° C. and for 1 hr at room temperature, the mixture was concentrated, triturated with water (50 ml) and extracted with diethylether (100 ml×3). The extract was washed with brine, dried and concentrated under reduced pressure to give (50) as a colorless oil. (3.7 g, quant.).

Workup

  1. stirringAfter stirring for 1 hr at -78° C. and for 1 hr at room temperature
  2. concentrationthe mixture was concentrated
  3. customtriturated with water (50 ml)
  4. extractionextracted with diethylether (100 ml×3)
  5. washThe extract was washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bdbb78adca2545028014cdfb5b2cca8f
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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