Tributyltin Chloride → HCID 58843572, compound

HRID 501906Notes

Reaction equation

HRID 501906 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:15]=[CH:14][C:10]2[CH:11]=[CH:12][O:13][C:9]=2[C:8]=1[CH3:16].Cl[Sn:18]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:27]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[C:12]1[O:13][C:9]2[C:8]([CH3:16])=[C:7]([CH3:6])[CH:15]=[CH:14][C:10]=2[CH:11]=1)[CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 10582912HCID 10582912, compoundHCID 178418339Butyllithium

Product 1

HCID 58843572HCID 58843572, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.5 M hexane (21 ml) of n-butyllithium was added dropwise to a solution of 6,7-dimethyl-benzofuran (4.1 g) in tetrahydrofuran (100 ml) at −78° C. under an argon atmosphere, and the mixture was stirred for half an hour. Then, chloro tri-n-butyltin (8.4 ml) was added to the mixture, and the mixture was stirred for one hour. Aqueous solution of saturated ammonium chloride was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (n-hexane) to obtain tri-n-butyl(6,7-dimethyl-benzofuran-2-yl) tin (10.8 g).

Workup

  1. stirringthe mixture was stirred for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (n-hexane)

Sources & evidence

ORD record
ord-c3678a221ac944da8c3bf30f894cb800
Source dataset
uspto-grants-2010_08
Patent number
US07772407B2

Reaction notes

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