Tributyltin Chloride → HCID 19751730, compound

HRID 483880Notes

Reaction equation

HRID 483880 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:31]([Sn:35](Cl)([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH3:34]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([Sn:35]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 19751739HCID 19751739, compoundHCID 178418339Butyllithium

Product 1

HCID 19751730HCID 19751730, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 1-3 (6.97 g, 17.5 mmoles) in THF (150 ml) was cooled to -75° C. and treated with n-butyl lithium (n-BuLi)(17.5 mmoles) dropwise. After stirring at -70° C. for 1 hr, tributyltin chloride (5.70 g, 17.5 mmol) was added dropwise. This was stirred at -70° C. for 2 hours and then overnight as the temperature was allowed to rise to ambient temperature. The solvent was subsequently removed and the residue was taken up in ether (500 ml), washed with H2O and brine, and dried with Na2SO4. Solvent removal gave 1-4 as a viscous oil.

Workup

  1. stirringThis was stirred at -70° C. for 2 hours
  2. customovernight
  3. customto rise to ambient temperature
  4. customThe solvent was subsequently removed
  5. washwashed with H2O and brine
  6. dry with materialdried with Na2SO4
  7. customSolvent removal

Sources & evidence

ORD record
ord-e1c9401053254e84a6391cb0e6f7e3cf
Source dataset
uspto-grants-1993_07
Patent number
US05227490

Reaction notes

Loading…