Tributyltin Chloride → HCID 23449307, compound

HRID 989832Notes

Reaction equation

HRID 989832 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[Si:30]([O:37][CH2:38][C:39]([C:41]1[N:42]=[CH:43][N:44]2[CH:48]=[CH:47][S:46][C:45]=12)=[O:40])([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].[Cl-].[NH4+]>C1COCC1>[Si:30]([O:37][CH2:38][C:39]([C:41]1[N:42]=[CH:43][N:44]2[C:48]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:47][S:46][C:45]=12)=[O:40])([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 17811075HCID 17811075, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23449307HCID 23449307, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butylstannyl chloride (2.97 ml) and 16.0 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added dropwise in that order to a solution of 2.37 g of 7-t-butyldimethylsilyloxyacetylimidazo[5,1-b]thiazole in 80 ml of THF in an argon atmosphere at −73° C. The mixture was stirred at the same temperature for 30 min. An ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 2:1). Of two main components, the fraction, which had been eluted earlier, was collected to give 484 mg of 7-t-butyldimethylsilyloxyacetyl-3-(tri-n-butylstannyl)-imidazo[5,1-b]thiazole.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 2:1)
  6. washOf two main components, the fraction, which had been eluted earlier
  7. customwas collected

Sources & evidence

ORD record
ord-d25840e37a7b4c82b674958de707f1cf
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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