1,4-Dioxane → HCID 53850438, compound

HRID 1651874Notes

Reaction equation

HRID 1651874 reaction equation
[C:1]1([S:7]([NH:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16](/[C:20](/[CH3:25])=[CH:21]\[C:22]([OH:24])=[O:23])[CH:17]=3)[CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCOC[CH2:27]1>[Ni]>[C:1]1([S:7]([NH:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:20]([CH3:25])[CH2:21][C:22]([O:24][CH3:27])=[O:23])[CH:17]=3)[CH2:12]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 70359813HCID 70359813, compound

Product 1

HCID 53850438HCID 53850438, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

3.2 g (8.95 mmol) of 3-(2-benzenesulphonamido-indan-5-yl)-crotonic acid in 50 ml of dioxan are hydrogenated in the presence of Raney nickel at room temperature under a hydrogen pressure of 3.5 bar. The mixture is filtered, the filtrate is evaporated, the residue is dissolved in 20 ml of methanol, and 1.5 ml of thionyl chloride are added dropwise at -50° C. The mixture is allowed to stand overnight at room temperature and is evaporated again, and the residue is chromatographed over silica gel using ethylene chloride. The fractions having an Rf-value of 0.6 are combined and evaporated. This gives a colourless oil.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated
  3. dissolutionthe residue is dissolved in 20 ml of methanol
  4. addition1.5 ml of thionyl chloride are added dropwise at -50° C
  5. customis evaporated again
  6. customthe residue is chromatographed over silica gel
  7. customevaporated
  8. customThis gives a colourless oil

Sources & evidence

ORD record
ord-7eb4afc7e8a545ad9f0b2ea098336272
Source dataset
uspto-grants-1990_05
Patent number
US04929754

Reaction notes

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