Cesium carbonate → HCID 67169636, compound

HRID 872895Notes

Reaction equation

HRID 872895 reaction equation
[O:1]=[C:2]([CH3:14])[CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]([O:11]CC)=[O:10])[CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)C.O>[O:1]=[C:2]([CH3:14])[CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 67170130HCID 67170130, compound

Product 1

HCID 67169636HCID 67169636, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 5-(2-oxopropyl)isoxazole-3-carboxylate (0.65 g, 3.30 mmol) was dissolved in ethanol (10 ml). A solution of cesium carbonate (1.611 g, 4.94 mmol) in water (5 ml) was added to the reaction mixture and it was stirred for 7 h at RT. The reaction mixture was concentrated, diluted with water and pH was adjusted to 2 with citric acid. The aqueous phase was extracted with ethyl acetate, dried with Na2SO4 and evaporated to dryness afforded 0.203 g (36%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ, 2.21 (s, 3H), 4.20 (s, 2H), 6.67 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water and pH
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ff62b4fc247b4e0aa7cd546a65bc81c8
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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