Dimethylformamide → 5-Fluoro-2-((R)-1-(oxiranylmethoxy)-phenyl]-ethanone

HRID 2407319Notes

Reaction equation

HRID 2407319 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.CC1C=CC(S([O:22][CH2:23][C@@H:24]2[O:26][CH2:25]2)(=O)=O)=CC=1.C(=O)([O-])[O-:28].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][CH2:5][C@:6]([CH2:8][CH:9]=[O:28])([O:22][CH2:23][CH:24]2[CH2:25][O:26]2)[CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 959922-Acetyl-4-fluorophenolHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 866447235-Fluoro-2-((R)-1-(oxiranylmethoxy)-phenyl]-ethanoneYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5′-fluoro-2′-hydroxyacetophenone (2.04 g, 13.25 mmol), (2R)-(−)-glycidyl tosylate (2.75 g, 12.05 mmol), potassium carbonate (2.16 g, 15.66 mmol) and N,N-dimethyl formamide (20 ml) was heated to 60° C. After 6 hours the reaction mixture was cooled down, water (20 ml) and ethyl acetate (20 ml) were added and the layers were separated. Organic phase was recovered and water layer was extracted twice with ethyl acetate. Organic phase and ethyl acetate extracts were combined and washed twice with water and evaporated to dryness. The crude product was crystallized from 2-propanol to yield 1.91 g (76%) of the pure title compound.

Workup

  1. temperatureAfter 6 hours the reaction mixture was cooled down
  2. customthe layers were separated
  3. customOrganic phase was recovered
  4. extractionwater layer was extracted twice with ethyl acetate
  5. washwashed twice with water
  6. customevaporated to dryness
  7. customThe crude product was crystallized from 2-propanol

Sources & evidence

ORD record
ord-269d7c2ebf044de685eb49962d652437
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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