Dimethyl Sulfoxide → HCID 10084622, compound

HRID 2286471Notes

Reaction equation

HRID 2286471 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:15])([C:12]([O-:14])=[O:13])C([O-])=O)[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[Na+].CS(C)=O.[C:28](OCC)(=O)[CH3:29]>O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:15])[C:12]([O:14][CH2:28][CH3:29])=[O:13])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 20493026HCID 20493026, compound

Product 1

HCID 10084622HCID 10084622, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 100 millimoles diethyl 2-(2-fluoro-4-biphenylyl)-methylmalonate VI, 110 millimoles sodium chloride, 200 millimoles water and 50 milliliters dimethyl sulfoxide is heated under nitrogen at about 130° to 180° C. for about 6 hours. On cooling the mixture is diluted with 100 milliliters water and 100 milliliters ethyl acetate. The layers are separated and the organic layer is washed two times with 25 milliliters of water. After drying over disodium sulfate the organic layer is concentrated in vacuo to give the desired ethyl 2-(2-fluoro-4-biphenylyl)propionate.

Workup

  1. temperatureis heated under nitrogen at about 130° to 180° C. for about 6 hours
  2. temperatureOn cooling the mixture
  3. customThe layers are separated
  4. washthe organic layer is washed two times with 25 milliliters of water
  5. dry with materialAfter drying over disodium sulfate the organic layer
  6. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-ce8a08a09b1e486186ef106a2fff5461
Source dataset
uspto-grants-1981_05
Patent number
US04266069

Reaction notes

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