Dimethyl Sulfoxide → HCID 57753244, compound

HRID 225615Notes

Reaction equation

HRID 225615 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:17]=[C:18]([F:20])[F:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(C)=O.O.[F-:26].[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][C:18]([F:26])([F:20])[F:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 522689Potassium FluorideHCID 57753432HCID 57753432, compound

Product 1

HCID 57753244HCID 57753244, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 0.71 mmol 5-(2,2-difluoro-vinyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester in 5 nml DMSO and 0.25 ml water was added 4.98 mmol potassium fluoride and the mixture was heated at 120° C. for 2 h. The mixture was cooled to room temperature and then taken up in THF and washed sequentially with water and with brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (48% yield). MS (m/e): 246.3 ([M+H−Me2C═CH2]+, 100%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed sequentially with water and with brine
  3. dry with materialThe organic phase was then dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-56e3fcf5461c4a10ad2aa2cc7cfb3d43
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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