Tributyltin Chloride → Cyclopropyltributylstannane

HRID 1690719Notes

Reaction equation

HRID 1690719 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH:15]1([Mg]Br)[CH2:17][CH2:16]1>C1COCC1>[CH2:1]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH:15]1[CH2:17][CH2:16]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 15096Tributyltin ChlorideHCID 178418630HCID 178418630, compound

Product 1

HCID 10947505Cyclopropyltributylstannane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tri-n-butyltin chloride (4 g, 11.8 mmol) in THF (20 mL) at 0° C. is added 0.5 M cyclopropylmagnesium bromide in THF (28.3 mL, 14.2 mmol). The reaction mixture is stirred under N2 at ambient temperature for 4 h and poured into pH 7 aqueous buffer. The resulting mixture is extracted with diethyl ether, washed with brine, dried over magnesium sulfate and filtered through sintered funnel. The filtrate is concentrated and the residue is distilled under vacuum to give tributylcyclopropyltin as a colorless oil which is used in the next step without further purification.

Workup

  1. additionpoured into pH 7 aqueous buffer
  2. extractionThe resulting mixture is extracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through sintered funnel
  6. concentrationThe filtrate is concentrated
  7. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-ff6ba616b0e34f4780df6de5ce2b2d29
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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