Tin tetrachloride → HCID 11036671, compound

HRID 1383631Notes

Reaction equation

HRID 1383631 reaction equation
[C:1]1([S:7]([CH:10]=[C:11]([O:30][Si](C(C)(C)C)(C)C)[C@H:12]([CH3:29])[C@@H:13]([CH3:28])[C@@H:14]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:15](OC)OC)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:1]1([S:7]([C:10]2[C:11](=[O:30])[C@H:12]([CH3:29])[C@@H:13]([CH3:28])[C@@H:14]([O:20][Si:21]([C:24]([CH3:27])([CH3:25])[CH3:26])([CH3:23])[CH3:22])[CH:15]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachloride2×HCID 516892Sodium BicarbonateHCID 54218465HCID 54218465, compound

Product 1

HCID 11036671HCID 11036671, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

The compound prepared in Example C4 (1.39 g, 2.43 mmol) was dissolved in anhydrous methylene chloride (30 ml) under an argon atmosphere. The solution was cooled to −78° C., and tin(IV) chloride (0.3 ml, 2.56 mmol) was dropwise added to the cooled solution. The reaction solution was stirred for one hr, tin(IV) chloride (0.6 ml, 5.12 mmol) was again dropwise added to the reaction solution, and the mixture was stirred for additional 2 hr. After the completion of the reaction, an aqueous sodium hydrogencarbonate solution was added thereto, and the temperature of the mixture was raised to room temperature, followed by separation. The organic layer was concentrated under reduced pressure, and the concentrate was then purified by column chromatographic separation on silica gel (toluene:ether=15:1) to give the title compound (0.87 g,91%).

Workup

  1. stirringthe mixture was stirred for additional 2 hr
  2. customAfter the completion of the reaction
  3. temperaturethe temperature of the mixture was raised to room temperature
  4. customfollowed by separation
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe concentrate was then purified by column chromatographic separation on silica gel (toluene:ether=15:1)

Sources & evidence

ORD record
ord-1b01c56477f54b8f958bd9e49643744c
Source dataset
uspto-grants-2001_07
Patent number
US06255339B1

Reaction notes

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