Trimethyltin chloride → HCID 131727685, compound

HRID 1822081Notes

Reaction equation

HRID 1822081 reaction equation
[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C([Mg]Cl)(C)C.C(C(CC=C)CO[SiH2]C1C=CC([Mg]Cl)=CC=1)C=C.[CH3:41][Sn:42](Cl)([CH3:44])[CH3:43]>O.C1COCC1>[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11]([Sn:42]([CH3:44])([CH3:43])[CH3:41])=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 14016Trimethyltin chlorideHCID 131727682HCID 131727682, compoundHCID 178418918HCID 178418918, compoundHCID 178443870HCID 178443870, compound

Product 1

HCID 131727685HCID 131727685, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

At first, a THF solution (2 mL) of the 4-(diallylethoxysilyl)iodobenzene (202 mg, 0.56 mmol) obtained in Example 2 was added dropwise with 2 mol/L of i-PrMgCl (0.59 mL (solvent: THF), 1.18 mmol) at −30° C. Then, the resultant solution was stirred under a nitrogen atmosphere at −30° C. for 1.5 hours to obtain a THF solution containing 4-(diallylethoxysilyl)phenylmagnesium chloride (Grignrad solution). Subsequently, the obtained Grignrad solution was added dropwise with 1 mol/L of trimethyl tin chloride (Me3SnCl: 1.18 mL (solvent: THF), 1.18 mmol) at −30° C. to obtain a reaction mixture. Thereafter, the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 13 hours, and added with distilled water to terminate the reaction. After that, the organic layer was separated from the reaction mixture, and the aqueous layer was extracted with ether to collect the organic layer. Subsequently, the organic layer thus collected was washed with sat.NaHCO3 and sat.NaCl, dried with MgSO4, filtered, and concentrated to obtain a crude product. Thereafter, the crude product thus obtained was separated and purified by silica gel column chromatography (hexane/EtOAc=5/1), and thereby 4-(diallylethoxysilyl)phenyl-trimethyltin was obtained (214 mg, 96% yield).

Workup

  1. customto obtain a reaction mixture
  2. customto terminate
  3. customthe reaction
  4. customAfter that, the organic layer was separated from the reaction mixture
  5. extractionthe aqueous layer was extracted with ether
  6. customto collect the organic layer
  7. customSubsequently, the organic layer thus collected
  8. washwas washed
  9. dry with materialNaCl, dried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto obtain a crude product
  13. customThereafter, the crude product thus obtained
  14. customwas separated
  15. custompurified by silica gel column chromatography (hexane/EtOAc=5/1)

Sources & evidence

ORD record
ord-1e6660a242294128a54fef16e1124648
Source dataset
uspto-grants-2009_10
Patent number
US07608673B2

Reaction notes

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