Trimethyltin chloride → Trimethyl (5-methyl-2-benzofuranyl)stannane

HRID 1034441Notes

Reaction equation

HRID 1034441 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH:13]=[CH:12][C:11]=2[CH:15]=1.[CH3:16][Sn:17](Cl)([CH3:19])[CH3:18]>C1COCC1>[CH3:16][Sn:17]([CH3:19])([CH3:18])[C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([CH3:6])=[CH:15][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 331035-MethylbenzofuranHCID 178418339Butyllithium

Product 1

HCID 85673465Trimethyl (5-methyl-2-benzofuranyl)stannaneYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (1.57M in hexane, 75 ml) was added dropwise to a stirred solution of 5-methylbenzofuran (14 g) in dry THF (150 ml) at -70° under nitrogen over 45 min. The solution was then allowed to warm to -55° before a solution of trimethyltin chloride (23 g) in THF (70 ml) was added dropwise. The solution temperature rose to -32°. The cooling bath was removed and the solution was stirred at room temperature for 2 h. The solution was diluted with ethyl acetate (250 ml) and washed with water (200 ml). The organic layer was dried and concentrated in vacuo to afford a yellow liquid (32 g). Kugelrohr distillation of this liquid gave the title compound (23.3 g) as a colourless liquid, b.p. 115° at 7 mbar.

Workup

  1. additionwas added dropwise
  2. customrose to -32°
  3. customThe cooling bath was removed
  4. additionThe solution was diluted with ethyl acetate (250 ml)
  5. washwashed with water (200 ml)
  6. customThe organic layer was dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-400980ffcf014dc18caf2aa99952806d
Source dataset
uspto-grants-1994_05
Patent number
US05317023

Reaction notes

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