Trimethyltin chloride → 5-Methyl-2-trimethylstannylbenzo[b]thiophene

HRID 618748Notes

Reaction equation

HRID 618748 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[CH3:11][Sn:12](Cl)([CH3:14])[CH3:13].[Cl-].[NH4+]>CCOCC.CCCCCC>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][C:7]([Sn:12]([CH3:14])([CH3:13])[CH3:11])=[CH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 14016Trimethyltin chlorideHCID 25517Ammonium ChlorideHCID 843465-Methylbenzo(b)thiophene

Product 1

HCID 218481335-Methyl-2-trimethylstannylbenzo[b]thiophene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

A solution of 7.411 g of 5-methylbenzo[b]thiophene (Maybridge, Chemical Co. Ltd., 11-78) in 35 ml of ether is added dropwise at 0° to a mixture of 40 ml of 1.5N butylithium in hexane and 40 ml of ether. After 30 minutes, a solution of 9.963 g of trimethyltin chloride in 50 ml of ether is also added dropwise at 0°. After stirring for 1 hour at 0°, 50 ml of 5% ammonium chloride solution are added. The product is obtained by extracting with 100 ml and 150 ml of ether. Distillation at 0.15 mbar and 100-106° yields 5-methyl-2-trimethylstannylbenzo[b]thiophene.

Workup

  1. customThe product is obtained
  2. extractionby extracting with 100 ml and 150 ml of ether
  3. distillationDistillation at 0.15 mbar and 100-106°

Sources & evidence

ORD record
ord-1a4a5670d88d41fb8cfb442a2c9a4b9e
Source dataset
uspto-grants-1999_09
Patent number
US05955487

Reaction notes

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