Imidazole → HCID 11276617, compound

HRID 1929788Notes

Reaction equation

HRID 1929788 reaction equation
[OH:1][CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[Si:10]([O:1][CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24827Acrylic acid, 2-(hydroxymethyl)-, ethyl esterHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11276617HCID 11276617, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.8 g of ethyl 2-(hydroxymethyl)acrylate (Organic Synthesis, Coll, Vol 8, 265, 1993) was diluted with 80 ml of N,N′-dimethylformamide, and 18.8 g of tert-butyldimethylsilyl chloride and 11.3 g of imidazole were added thereto. The resulting mixture was incubated at room temperature for two hours. After the reaction terminated, water was added, and the resulting solution was extracted with ethyl acetate. The organic layer was washed five times with water and saturated chloride water, dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate:n-hexane=1:30) to obtain the title compound (14.7 g, 73%).

Workup

  1. additionwere added
  2. customAfter the reaction terminated
  3. additionwater was added
  4. extractionthe resulting solution was extracted with ethyl acetate
  5. washThe organic layer was washed five times with water and saturated chloride water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationdistilled under a reduced pressure
  9. customThe resulting residue was purified by column chromatography (ethyl acetate:n-hexane=1:30)

Sources & evidence

ORD record
ord-497840b4ca644aa0af55e0f6d2a6b721
Source dataset
uspto-grants-2012_05
Patent number
US08188102B2

Reaction notes

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