Water → HCID 67458894, compound

HRID 1051864Notes

Reaction equation

HRID 1051864 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[O:13]1COCO[CH2:14]1.O>CS(C)=O.C[O-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][OH:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 80811,3,5-TrioxaneHCID 2733233Methyl 2-(4-fluorophenyl)acetate

Product 1

HCID 67458894HCID 67458894, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of methyl (4-fluorophenyl)acetate (5.5 g) in DMSO (220 mL) was added 1,3,5-trioxane (3.24 g) and sodium methoxide (88 mg). The mixture was stirred at room temperature for 16 h. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silicagel chromatography gave 3.8 g of the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried (sodium sulfate)
  4. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-68fe8d99b3d24c809afed5eb545c238e
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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