Tributyltin Chloride → HCID 17756360, compound

HRID 2120780Notes

Reaction equation

HRID 2120780 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23]>C(COC)OC>[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 17756360HCID 17756360, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A mixture of 15.85 g (0.0837 mole) of 1-benzyl-4-piperidone in 140 ml of anhydrous dimethoxyethane and g (0.0837 mole) of trisilidrazine in 140 ml of anhydrous dimethoxyethane is stirred at room temperature for 3 hours. The solvent is evaporated off under reduced pressure. The residue is taken up into 420 ml of anhydrous hexane and 420 ml of anhydrous tetramethylethylenediamine are added thereto. The mixture is cooled to −78° C. and 156 ml of n-butyllithium (0.25 mole)(1.6 M solution in hexane) are added dropwise thereto. After about 30 minutes the temperature is allowed to attain 0° C. and stirring is effected for 15 minutes. 45 ml (0.167 mole) of tributylstannyl chloride are then added to the reaction mixture. After 1 hour, a water/ice mixture is added with extreme caution. Extraction is carried out with ethyl ether, the organic phase is washed with water, drying is effected over sodium sulphate and the solvent is evaporated off under reduced pressure. 70 g of crude product are obtained which are purified by silica gel column chromatography in eluting with a cyclohexane/ethyl acetate mixture=95/5. The title compound is obtained as an oil.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. additionare added
  3. temperatureThe mixture is cooled to −78° C.
  4. waitAfter about 30 minutes the temperature is allowed
  5. customto attain 0° C.
  6. stirringstirring
  7. waitis effected for 15 minutes
  8. waitAfter 1 hour
  9. extractionExtraction
  10. washthe organic phase is washed with water
  11. customdrying
  12. customthe solvent is evaporated off under reduced pressure
  13. custom70 g of crude product are obtained which
  14. customare purified by silica gel column chromatography
  15. washin eluting with a cyclohexane/ethyl acetate mixture=95/5

Sources & evidence

ORD record
ord-4935eb1bd8c042eca9c18dfc9b75e189
Source dataset
uspto-grants-2004_02
Patent number
US06693118B2

Reaction notes

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