Cesium carbonate → 860371-76-2

HRID 872542Notes

Reaction equation

HRID 872542 reaction equation
[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([C:10]([O:12]CC)=[O:11])[CH:6]=1)([CH3:4])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+]>CO.O>[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([C:10]([OH:12])=[O:11])[CH:6]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 16764416HCID 16764416, compound

Product 1

HCID 67168640860371-76-2Yield 65.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 5-(2-hydroxypropan-2-yl)isoxazole-3-carboxylate (0.436 g, 2.189 mmol) was dissolved in methanol (20 ml). A solution of cesium carbonate (1.426 g, 4.38 mmol) in 20 ml of water was added and the reaction mixture was stirred at RT for 18 h. Solvents were evaporated and the residue was taken into a mixture of ethyl acetate and water, pH was adjusted to 2.5 with 10% citric acid solution and the layers were separated. Water layer was extracted three times with ethyl acetate and the combined organic layers were dried with Na2SO4, filtered and evaporated affording 0.246 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.49 (s, 6H), 5.75 (m, 1H), 6.60 (s, 1H).

Workup

  1. customSolvents were evaporated
  2. additionthe residue was taken into a mixture of ethyl acetate and water, pH
  3. customthe layers were separated
  4. extractionWater layer was extracted three times with ethyl acetate
  5. dry with materialthe combined organic layers were dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-eb513e94f7ba4791a3b2fc7e29f930c1
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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