Chlorotrimethylsilane → HCID 54480533, compound

HRID 231338Notes

Reaction equation

HRID 231338 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9](=[O:11])[CH3:10])[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.Cl[Si:20]([CH3:23])([CH3:22])[CH3:21]>C(#N)C>[CH3:1][O:2][N:3]=[C:4]([C:9]([O:11][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH2:10])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 54071723HCID 54071723, compound

Product 1

HCID 54480533HCID 54480533, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 15 ml of acetonitrile was dissolved 795 mg of methyl 2-methoxyimino-3-oxobutyrate, followed by addition of 2.1 ml of triethylamine. Then, 1.9 ml of chlorotrimethylsilane was added dropwise with ice-cooling and the mixture was stirred at 20°-25° C. for 1 hour for silylation. The reaction mixture was concentrated under reduced pressure and the residue was suspended in 10 ml of carbon tetrachloride and the suspension was filtered in a nitrogen gas stream to remove insolubles. The filtrate was concentrated under reduced pressure to give 1.00 g of methyl 2-methoxyimino-3-trimethylsilyloxy-3-butenoate as oil. Yield 86.5%.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationthe suspension was filtered in a nitrogen gas stream
  4. customto remove insolubles
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-94e84c4f6df84066bffd9ad9e493bf86
Source dataset
uspto-grants-1989_07
Patent number
US04845257

Reaction notes

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