Dimethyl Sulfoxide → HCID 58047164, compound

HRID 1888737Notes

Reaction equation

HRID 1888737 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16](F)[CH:15]=2)=[CH:8][CH:7]=1)[CH3:4].[OH2:23].C[S:25]([CH3:27])=O>>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]3[CH:18]=[C:27]([C:6]([O:5][CH2:3][CH3:4])=[O:23])[S:25][C:16]=3[CH:15]=2)=[CH:8][CH:7]=1)[CH3:4]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 24758Sodium hydrideHCID 58047174HCID 58047174, compound

Product 1

HCID 58047164HCID 58047164, compoundYield 63%

Procedure

To a solution of ethyl mercaptoacetateester (0.450 mL, 4.07 mmol) in DMSO (10 mL) was added sodium hydride (60%, 196 mg, 4.89 mmol) and the mixture was stirred at room temperature for 10 min. To this reaction mixture was added 4-[2-(4-ethoxyphenyl)ethyl]-2-fluorobenzaldehyde (886 mg, 3.26 mmol) obtained in Reference Example 171, and the mixture was stirred at room temperature for 20 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=19:1 to 1:1) to give the title compound (723 mg, yield 63%) as an oil.

Workup

  1. customobtained in Reference Example 171
  2. stirringthe mixture was stirred at room temperature for 20 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed twice with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=19:1 to 1:1)

Sources & evidence

ORD record
ord-9bbd83f35b104ae2ab7296cc7b60e05b
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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