1,4-Dioxane → HCID 53850438, compound

HRID 620209Notes

Reaction equation

HRID 620209 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-72197b1366b84834b0e4ffafa16ad398
Source dataset
uspto-grants-1989_04
Patent number
US04820705

Reaction notes

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