2-(4-Methylisoxazol-3-yl)ethanol → 2-(4-Methyl-1,2-oxazol-3-yl)acetic acid

HRID 1771957Notes

Reaction equation

HRID 1771957 reaction equation
[CH3:1][C:2]1[C:3]([CH2:7][CH2:8][OH:9])=[N:4][O:5][CH:6]=1.CC(C)=[O:12].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.OS([O-])=O.[Na+].CCOC(C)=O>[CH3:1][C:2]1[C:3]([CH2:7][C:8]([OH:12])=[O:9])=[N:4][O:5][CH:6]=1

Participants

6

Reactant 2

HCID 900798382-(4-Methylisoxazol-3-yl)ethanolHCID 131709961Jones' reagent

Product 1

HCID 693006392-(4-Methyl-1,2-oxazol-3-yl)acetic acidYield 77%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolventHCID 23665763Sodium BisulfiteSolvent

Procedure

To a solution of 2-(4-methylisoxazol-3-yl)ethanol, Intermediate S7A, (7 mg, 0.055 mmol) in acetone (Volume: 0.5 mL) at room temperature was added 1.35M Jones reagent (0.082 mL, 0.110 mmol). The reaction mixture was stirred at room temperature for 5 h. The mixture was diluted with 2% NaHSO3 and EtOAc. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to afford 2-(4-methylisoxazol-3-yl)acetic acid, Intermediate S7B (6 mg, 0.043 mmol, 77% yield). 1H NMR (400 MHz, chloroform-d) δ 8.18 (s, 1H), 3.80 (s, 2H), 2.04 (s, 3H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf1a9be49f7242dcb6ef264707422180
Source dataset
uspto-grants-2016_02
Patent number
US09249157B2

Reaction notes

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