Tributyltin Chloride → HCID 23448993, compound

HRID 989854Notes

Reaction equation

HRID 989854 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C:12]1[N:13]=[C:14]([CH3:20])[N:15]2[CH:19]=[CH:18][S:17][C:16]=12)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[Cl-].[NH4+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Si:1]([O:8][CH2:9][C:10]([C:12]1[N:13]=[C:14]([CH3:20])[N:15]2[CH:19]=[C:18]([Sn:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])[S:17][C:16]=12)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23449105HCID 23449105, compoundHCID 23714775LiHMDS tetrahydrofuran2×

Product 1

HCID 23448993HCID 23448993, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

7-t-Butyldimethylsilyloxyacetyl-5-methylimidazo-[5,1-b]thiazole (49.5 mg) was dissolved in 2 ml of THF and 0.4 ml of HMPA. Tri-n-butylstannyl chloride (0.059 ml) and 0.319 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added dropwise in that order to the solution in an argon atmosphere at −73° C. The mixture was stirred at the same temperature for one hr. A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (0.160 ml) was added dropwise thereto. The mixture was stirred at the same temperature for additional 40 min. An ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate and washing three times with brine. 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 give 66.9 mg of the title compound.

Workup

  1. stirringThe mixture was stirred at the same temperature for additional 40 min
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing three times with brine
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-5848c8289d624f3388f5b58fb61b2e32
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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