O-Cresol → HCID 59577052, compound

HRID 2041969Notes

Reaction equation

HRID 2041969 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CS(O[CH:16]1[CH2:19][N:18]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17]1)(=O)=O>CN(C=O)C>[C:21]1([C:20]([N:18]2[CH2:19][CH:16]([O:7][C:6]3[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=3[CH3:8])[CH2:17]2)=[O:27])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 335O-CresolHCID 24758Sodium hydrideHCID 11448209HCID 11448209, compound

Product 1

HCID 59577052HCID 59577052, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of o-cresol (0.16 g, 1.51 mmol) in DMF (10 ml) was added 60% sodium hydride (0.063 g, 1.59 mmol) at room temperature. After 10 min 1-benzoylazetidin-3-yl methanesulfonate (0.50 g, 1.96 mmol) was added and the resulting reaction mixture was heated at 60° C. for 16 h. After this reaction mixture was cooled to room temperature, partitioned between ethyl acetate and water and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 80:20 to 50:50, heptane/ethyl acetate) to provide a white solid. Trituration of the solid with heptane/ethyl acetate and collection of the resulting solids by filtration provided phenyl(3-(o-tolyloxy)azetidin-1-yl)methanone (0.14 g, 35%) as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. temperatureAfter this reaction mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. customseparated
  5. washThe organic layer was washed with saturated sodium chloride
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography (silica gel, 80:20 to 50:50, heptane/ethyl acetate)
  10. customto provide a white solid
  11. customTrituration of the solid with heptane/ethyl acetate and collection of the resulting solids
  12. filtrationby filtration

Sources & evidence

ORD record
ord-3cf3c9e3e16740fcb69a3fdf6f02de92
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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