Sodium Chloride → Ethyl 5-tert-butyl-1,2-oxazole-3-carboxylate

HRID 2261290Notes

Reaction equation

HRID 2261290 reaction equation
[C:1]([C:5]#[CH:6])([CH3:4])([CH3:3])[CH3:2].Cl/[C:8](=[N:14]/[OH:15])/[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C.[Cl-].[Na+]>O1CCCC1>[C:1]([C:5]1[O:15][N:14]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 16765306Ethyl 5-tert-butyl-1,2-oxazole-3-carboxylateYield 15.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.61 g of t-butylacetylene and 9.09 g of ethyl (2E)-chloro(hydroxyimino)acetate were dissolved in 70 ml of tetrahydrofuran, and 11.4 ml of triethylamine was then added dropwise at 0° C. over 30 minutes. The mixture was stirred at room temperature overnight. After aqueous saturated sodium chloride was added, the reaction mixture was separated into layers. The aqueous layer was extracted with methyl-t-butyl ether. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.83 g of ethyl 5-t-butyl-isoxazole-3-carboxylate.

Workup

  1. customthe reaction mixture was separated into layers
  2. extractionThe aqueous layer was extracted with methyl-t-butyl ether
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-931765df27ca44b4bfb8ae90ac832450
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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