Trimethyltin chloride → HCID 17983299, compound

HRID 1270425Notes

Reaction equation

HRID 1270425 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=[CH:2]1.C([Li])CCC.[CH3:16][Sn:17](Cl)([CH3:19])[CH3:18].[F-].[K+]>O1CCCC1.CCCCCC>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=[C:2]1[Sn:17]([CH3:19])([CH3:18])[CH3:16]

Participants

7

Reactant 4

HCID 14016Trimethyltin chlorideHCID 1360711,4-BenzodioxinHCID 522689Potassium FluorideHCID 178418339Butyllithium

Product 1

HCID 17983299HCID 17983299, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

14.91 mmol of 1,4-benzodioxine are dissolved in 18 ml of anhydrous tetrahydrofuran under an anhydrous atmosphere, and the temperature of the solution is lowered to −78° C. 23.86 mmol of a 1.5M solution of n-butyllithium in hexane are added dropwise to the reaction mixture, which is stirred at −78° C. for 2 hours 15 minutes. 37.28 mmol of trimethyltin chloride dissolved in 10 ml of anhydrous tetrahydrofuran are added dropwise and the reaction mixture is stirred at −78° C. for 45 minutes and then returned to ambient temperature for 15 hours. The reaction mixture is hydrolysed with 15% aqueous potassium fluoride solution and is stirred for 45 minutes. The precipitated tin salts are removed by filtration, and the aqueous phase is extracted 3 times with ethyl acetate. The organic phases are combined and concentrated. Purification by flash chromatography over silica gel (petroleum ether/ethyl acetate: 95/5) allows the expected product to be obtained.

Workup

  1. customis lowered to −78° C
  2. additionare added dropwise
  3. stirringthe reaction mixture is stirred at −78° C. for 45 minutes
  4. waitreturned to ambient temperature for 15 hours
  5. stirringis stirred for 45 minutes
  6. customThe precipitated tin salts are removed by filtration
  7. extractionthe aqueous phase is extracted 3 times with ethyl acetate
  8. concentrationconcentrated
  9. customPurification by flash chromatography over silica gel (petroleum ether/ethyl acetate: 95/5)
  10. customto be obtained

Sources & evidence

ORD record
ord-48a0d73502fb4fc1811bafe51fea8471
Source dataset
uspto-grants-2007_04
Patent number
US07202255B2

Reaction notes

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