Methanol → HCID 67170130, compound

HRID 872894Notes

Reaction equation

HRID 872894 reaction equation
[OH:1][CH:2]([CH3:14])[CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CO.O>CC(C)=O>[O:1]=[C:2]([CH3:14])[CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 67168642HCID 67168642, compoundHCID 131709961Jones' reagent

Product 1

HCID 67170130HCID 67170130, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-(2-hydroxypropyl)isoxazole-3-carboxylate (1.5 g, 7.53 mmol) was dissolved in acetone (40 ml) and cooled to 0° C. Jones' reagent (5.90 ml, 7.91 mmol) was added dropwise and the reaction mixture was stirred at 0 C for 30 min. Then the reaction mixture was allowed to warm up to RT and stirred 18 h. Mixture of methanol (30 ml) and water (30 ml) was added and then the volatiles were evaporated. The residue was extracted with DCM, dried with Na2SO4 and evaporated to dryness to afford 1.38 g (93%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): 6, 1.32 (t, 3H), 2.22 (s, 3H), 4.29-4.44 (m, 2H), 4.22 (s, 2H), 6.67 (s, 1H).

Workup

  1. temperatureto warm up to RT
  2. stirringstirred 18 h
  3. additionwas added
  4. customthe volatiles were evaporated
  5. extractionThe residue was extracted with DCM
  6. dry with materialdried with Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-dad9accdc9b849ee8b5bf9697291b985
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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