Sodium Iodide → HCID 54211206, compound

HRID 231339Notes

Reaction equation

HRID 231339 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9](=[O:11])[CH3:10])[C:5]([O:7][CH3:8])=[O:6].[I-].[Na+].C(N(CC)CC)C.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>C(#N)C>[Si:25]([O:11][C:9](=[CH2:10])[C:4](=[N:3][O:2][CH3:1])[C:5]([O:7][CH3:8])=[O:6])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 54071723HCID 54071723, compound

Product 1

HCID 54211206HCID 54211206, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In 20 ml of acetonitrile were dissolved 795 mg of methyl 2-methoxyimino-3-oxobutyrate and 2.25 g of sodium iodide, followed by addition of 2.1 ml of triethylamine. Then, a solution of 1.13 g tert-butyldimethylchlorosilane in 10 ml acetonitrile was added dropwise and the mixture was refluxed for 6.5 hours. The reaction mixture was concentrated under reduced pressure and 20 ml of hexane and 20 ml of water were added to dissolve the residue. The organic layer was separated, washed with 20 ml of 5% aqueous sodium hydrogen carbonate solution, 20 ml of 1N hydrochloric acid and 20 ml of water in the order mentioned, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column and elution was carried out with 100 ml of hexane-ether (5:1, v/v). The eluate was concentrated under reduced pressure to give methyl 3-tert-butyldimethylsilyloxy-2-methoxyimino-3-butenoate as oil.

Workup

  1. temperaturethe mixture was refluxed for 6.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure and 20 ml of hexane and 20 ml of water
  3. additionwere added
  4. dissolutionto dissolve the residue
  5. customThe organic layer was separated
  6. washwashed with 20 ml of 5% aqueous sodium hydrogen carbonate solution, 20 ml of 1N hydrochloric acid and 20 ml of water in the order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on a silica gel column and elution
  10. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1075bd6e7804b149ac6c614289d7d9c
Source dataset
uspto-grants-1989_07
Patent number
US04845257

Reaction notes

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