HCID 57316763, compound → HCID 9890046, compound

HRID 650581Notes

Reaction equation

HRID 650581 reaction equation
[CH3:1][C:2]1[C:3]([CH:16]([O:18][C:19]2[CH:32]=[CH:31][C:22]([CH:23]=[C:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:20]=2)[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1>O1CCOCC1.[Pd]>[CH3:1][C:2]1[C:3]([CH:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:31][CH:32]=2)[CH3:17])=[CH:4][C:5]2[C:6]([CH3:14])([CH3:15])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 57316763HCID 57316763, compound

Product 1

HCID 9890046HCID 9890046, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-(4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphtalen-2-yl)-ethoxy)-benzylidene)-thiazolidine-2,4-dione (200 mg; 0.44 mmol) was first attempted hydrogenated with Pd/C 5% (235 mg) in dioxane (50 ml) at 100° C. for 10 hours. Filtration and extraction of the mixture showed a mixture of starting material and product (185 mg). The mixture was then dissolved in MeOH (25 ml) and magnesium (100 mg) was added. The reaction mixture was stirred over the week end at room temperature and then evaporated. The residue was dissolved in water and ethyl acetate and the pH was adjusted to 7 with 1 N HCl. The mixture was stirred for 5 minutes after which the organic phase was separated. The organic phase was dried and evaporated, and the residue was purified on column chromatography using methylene chloride: methanol (15:1) as eluent to give the title compound in 76 mg (38%) yield. Compound 1.

Workup

  1. filtrationFiltration and extraction of the mixture
  2. additiona mixture of starting material and product (185 mg)
  3. dissolutionThe mixture was then dissolved in MeOH (25 ml)
  4. additionmagnesium (100 mg) was added
  5. customevaporated
  6. dissolutionThe residue was dissolved in water
  7. stirringThe mixture was stirred for 5 minutes after which the organic phase
  8. customwas separated
  9. customThe organic phase was dried
  10. customevaporated
  11. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-39d7ac91f5874a78852995910b039f9c
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Reaction notes

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