Water → HCID 73667681, compound

HRID 2372432Notes

Reaction equation

HRID 2372432 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=[C:16]3[S:21][CH2:20][CH2:19][CH2:18][S:17]3)[CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[OH2:24]>O1CCCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:14](=[C:16]3[S:17][CH2:18][CH2:19][CH2:20][S:21]3=[O:24])[CH3:15])=[CH:12][CH:13]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 962WaterHCID 14674056HCID 14674056, compound

Product 1

HCID 73667681HCID 73667681, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[1-{4-(4-Methoxyphenoxy)phenyl}ethan-1-ylidene]-1,3-dithiane, 5 g, was dissolved in a solvent mixture of 100 ml of tetrahydrofuran and 50 ml of methanol and, 15 g of an aqueous solution containing 2.45 g of oxon was dropwise added to the solution under ice cooling. After stirring for an hour at the same temperature, water was added to the reaction mixture followed by extraction with chloroform. The organic phase was washed with a sodium thiosulfate aqueous solution and then with water. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride) to give 0.85 g of white crystals.

Workup

  1. additioncontaining 2.45 g of oxon
  2. additionwas dropwise added to the solution under ice cooling
  3. additionwas added to the reaction mixture
  4. extractionfollowed by extraction with chloroform
  5. washThe organic phase was washed with a sodium thiosulfate aqueous solution
  6. dry with materialAfter drying over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-583fab7f487f42cca87e31b636f158d5
Source dataset
uspto-grants-1992_03
Patent number
US05098928

Reaction notes

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