Tributyltin Chloride → HCID 59155929, compound

HRID 1662869Notes

Reaction equation

HRID 1662869 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[C:13]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][S:11][C:10]=1[C:22]1[S:23][CH:24]=[C:25]([P:35]([O:40][CH2:41][CH3:42])([O:37][CH2:38][CH3:39])=[O:36])[C:26]=1[P:27]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH2:43]([Li])[CH2:44][CH2:45][CH3:46].[CH2:48]([Sn:52](Cl)([CH2:57][CH2:58][CH2:59][CH3:60])[CH2:53][CH2:54][CH2:55][CH3:56])[CH2:49][CH2:50][CH3:51].P([O-])([O-])(O)=O.[Na+].[Na+].S(O)(O)(=O)=O.[Na]>C1COCC1>[CH2:43]([Sn:52]([CH2:53][CH2:54][CH2:55][CH3:56])([CH2:48][CH2:49][CH2:50][CH3:51])[C:24]1[S:23][C:22]([C:10]2[S:11][C:12]([Sn:52]([CH2:57][CH2:58][CH2:59][CH3:60])([CH2:53][CH2:54][CH2:55][CH3:56])[CH2:48][CH2:49][CH2:50][CH3:51])=[C:13]([P:14]([O:16][CH2:17][CH3:18])([O:19][CH2:20][CH3:21])=[O:15])[C:9]=2[P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])=[C:26]([P:27]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28])[C:25]=1[P:35]([O:37][CH2:38][CH3:39])([O:40][CH2:41][CH3:42])=[O:36])[CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 86638409HCID 86638409, compound2×HCID 131729223HCID 131729223, compoundHCID 178418339Butyllithium

Product 1

HCID 59155929HCID 59155929, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In 25 ml of THF, 0.952 g (1.34 mmols) of the 3,3′,4,4′-tetrakis(diethoxyphosphoryl)-[2,2′]-bithiophene obtained in Example 6(8) or (9) was dissolved, and cooled down to −78° C. Commercially available n-butyl lithium (1.59 M hexane solution, 5.34 mmols) was slowly dropped, followed by stirring for 3 hours at a standing temperature. Thereafter, 1.956 g (6.01 mmols) of commercially available tributylstannyl chloride was dropped and stirred for 4 hours. After completion of the reaction, a disodium hydrogen phosphate/sodium dihydrogen sulfate buffer solution, adjusted to pH=7, was added to complete the reaction, followed by extraction with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed, and the resulting crude product was purified with a silica gel column (ethyl acetate) to obtain the specified substance in the form of a transparent oil at a yield of 1.174 g (yield: 68%). The thus obtained substance was used as it is for reaction in Example 6(11).

Workup

  1. stirringstirred for 4 hours
  2. customAfter completion of the reaction
  3. additionwas added
  4. customthe reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic phase was washed with a saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed
  9. customthe resulting crude product was purified with a silica gel column (ethyl acetate)
  10. customto obtain the specified substance in the form of a transparent oil at a yield of 1.174 g (yield: 68%)
  11. customis for reaction in Example 6(11)

Sources & evidence

ORD record
ord-195ad81711764e55ae0d767f92ac1389
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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