Tributyltin Chloride → HCID 21400915, compound

HRID 973113Notes

Reaction equation

HRID 973113 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][Li])=[CH:5][CH:4]=1.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15].[Cl-].[NH4+]>CCCCCC.C1COCC1.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][Sn:16]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 178506885HCID 178506885, compound

Product 1

HCID 21400915HCID 21400915, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

Using the apparatus and procedure of Example I, 100 ml. of an approximately one-molar solution of (p-methoxyphenylthio)methyllithium in hexane-THF solvent is added dropwise with stirring to 0.1 mole of tributyltin chloride dissolved in THF. The temperature is maintained by means of an ice bath in the range of from 0° C to 10° C. Following the complete addition over a one-quarter hour period, the reaction mixture is stirred for two hours at room temperature and hydrolyzed by pouring into aqueous one-molar ammonium chloride. Extraction from the hydrolyzate with ether solvent and purification by vacuum distillation yields the desired product, (p-methoxyphenylthiomethyl)tributyltin.

Workup

  1. temperatureThe temperature is maintained by means of an ice bath in the range of from 0° C to 10° C
  2. additionthe complete addition over a one-quarter hour period
  3. extractionExtraction from the hydrolyzate
  4. customwith ether solvent and purification
  5. distillationby vacuum distillation

Sources & evidence

ORD record
ord-b2e0a14de99c4724bf0f4988ea19134f
Source dataset
uspto-grants-1977_10
Patent number
US04055413

Reaction notes

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