Tributylstannane → Methallyltri-n-butyltin

HRID 1357499Notes

Reaction equation

HRID 1357499 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].Br[CH2:27][C:28]([CH3:30])=[CH2:29]>C1COCC1>[CH3:29][C:28](=[CH2:27])[CH2:30][Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 7912DiisopropylamineHCID 3577853-Bromo-2-methyl-1-propeneHCID 178418339Butyllithium

Product 1

HCID 11013379Methallyltri-n-butyltinYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (16.5 mL of a 2.5 M hexanes solution, 41.2 mmol)was added to a 0° C. solution of diisopropylamine (5.4 mL, 41.3 mmol) in THF (40 mL). After stirring for 5 minutes, tributyltin hydride (10 g, 34.4 mmol) was added. After stirring for 15 minutes at 0° C., the reaction mixture was cooled to −78° C. and 3-bromo-2-methylpropene (4.0 mL, 39.7 mmol) was added dropwise. After stirring for an additional hour, the cold reaction mixture was quenched with dilute ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate layer was dried (MgSO4), filtered and concentrated to afford a colorless liquid, 2-methylallyl tributyltin (11.6 g, 98%) which was used without purification for the next step.

Workup

  1. stirringAfter stirring for 15 minutes at 0° C.
  2. stirringAfter stirring for an additional hour
  3. customthe cold reaction mixture
  4. customwas quenched with dilute ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-49e350a24f5045468f17645b6d48838e
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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