Imidazole → Ethyl 5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazole-3-carboxylate

HRID 2261345Notes

Reaction equation

HRID 2261345 reaction equation
[OH:1][CH:2]([C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1)[CH3:3].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>CN(C)C=O>[Si:19]([O:1][CH:2]([C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1)[CH3:3])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 12920231Ethyl 5-(1-Hydroxyethyl)isoxazole-3-carboxylate

Product 1

HCID 57736274Ethyl 5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazole-3-carboxylateYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.55 g of ethyl 5-(1-hydroxyethyl)-isoxazole-3-carboxylate was dissolved in 30 ml of N,N-dimethylformamide, and 2.38 g of imidazole and 5.28 g of t-butyldimethylsilyl chloride were then added. The mixture was stirred at room temperature for 10 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to obtain 8.95 g of ethyl 5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazole-3-carboxylate.

Workup

  1. extractionthe reaction mixture was extracted with methyl-t-butyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df70b49f59e64e4c93c1ba8950d81774
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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