Triacetoxyperiodinane → 1-[3-(4-Fluorophenyl)-1,2-oxazol-5-yl]ethan-1-one

HRID 2406487Notes

Reaction equation

HRID 2406487 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13]([OH:15])[CH3:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86680476HCID 86680476, compound

Product 1

HCID 228319891-[3-(4-Fluorophenyl)-1,2-oxazol-5-yl]ethan-1-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-(4-fluorophenyl)isoxazol-5-yl)ethanol (0.15 g, 0.724 mmol) in DCM (10 mL) was added Dess-Martin periodinane (0.46 g, 1.08 mmol) at room temperature. The resulting solution was stirred for 16 h. The reaction mixture was filtered and washed with DCM (3×50 mL). The organic layer was washed with water (50 mL) followed by brine solution (50 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain crude product. The crude product was purified by silica gel column chromatography (100-200 mesh; using 80% ethyl acetate in hexane) to obtain 1-(3-(4-fluorophenyl)isoxazol-5-yl)ethanone as off-white solid (0.1 g, 68% yield). 1H NMR (400 MHz, CDCl3): δ 7.81 (t, 2H), 7.20 (s, 1H), 7.17 (d, 2H), 2.66 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DCM (3×50 mL)
  3. washThe organic layer was washed with water (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain crude product
  7. customThe crude product was purified by silica gel column chromatography (100-200 mesh; using 80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b65d8b371a254c578d563a43df33b892
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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