Trimethylsilyldiazomethane → 2-(4-Fluorophenyl)oxazol-4(5H)-one

HRID 538416Notes

Reaction equation

HRID 538416 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]=[C:9]=[O:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.O>[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]2[O:7][CH2:13][C:9](=[O:10])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27333754-Fluorobenzoyl isocyanate

Product 1

HCID 468639972-(4-Fluorophenyl)oxazol-4(5H)-oneYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluorobenzoyl isocyanate (1.2 g, 7.2 mmol) in DCM (25 mL) was added (trimethylsilyl)diazomethane (2.0 M in hexane, 4.3 mL, 8.6 mmol) at 0° C. The reaction mixture was stirred for 45 min at rt. The mixture was diluted with water and the separated aqueous phase was extracted with DCM (3×). The combined organic layers were dried over (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 100:0-80:20 DCM-methanol) to afford 870 mg of 2-(4-fluorophenyl)oxazol-4(5H)-one: LCMS (m/z): 180.0 (MH+), tR=0.39 min

Workup

  1. extractionthe separated aqueous phase was extracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried over (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (SiO2, 100:0-80:20 DCM-methanol)

Sources & evidence

ORD record
ord-e0650791fb2343e2a35e7626dcb0533c
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Reaction notes

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