Sodium Methoxide → HCID 178458866, compound

HRID 477409Notes

Reaction equation

HRID 477409 reaction equation
[C:1]([C:5]1[C:6](=[O:27])[CH2:7][CH:8]([C:12]2[C:17]([CH3:18])=[C:16]([N+:19]([O-])=O)[C:15]([CH3:22])=[C:14]([C:23](=[O:25])[CH3:24])[C:13]=2[CH3:26])[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].C[O-].[Na+].[H][H]>CO.[Pd]>[C:1]([C:5]1[C:6](=[O:27])[CH2:7][CH:8]([C:12]2[C:17]([CH3:18])=[C:16]([NH2:19])[C:15]([CH3:22])=[C:14]([C:23](=[O:25])[CH3:24])[C:13]=2[CH3:26])[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compoundHCID 178458852HCID 178458852, compound

Product 1

HCID 178458866HCID 178458866, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred solution of 2-propionyl-3-hydroxy-5-[3-acetyl-5-nitro-2,4,6-trimethylphenyl]cyclohex-2-en-1-one (4.2 g, 11.3 mmol) and sodium methoxide (0.61 g, 11.3 mmol) in methanol (80 ml) was hydrogenated at atmospheric pressure over 10% palladium on charcoal (0.3 g). After uptake of hydrogen ceased the solution was neutralized and the methanol was removed under reduced pressure. The residue was partitioned between water and methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (elution with an increasing gradient of methanol in methylene chloride) to yield 2-propionyl-3-hydroxy-5-(3-acetyl-5-amino-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a red brown solid (3.28 g, 85%) the compound was characterized by proton magnetic resonance spectroscopy (CDCl3, δ in ppm): 1.18 (3H,t ; 2.0 3H,s); 2.12 (3H,s); 2.18 (3H,s ; 2.40 3H,s); 2.4-4.1 (5H,m); 3.07 (2H,q); 3.6 (2H, brs); 18.05 (1H,brs).

Workup

  1. customthe methanol was removed under reduced pressure
  2. customThe residue was partitioned between water and methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by chromatography on silica gel (
  7. washelution with an increasing gradient of methanol in methylene chloride)

Sources & evidence

ORD record
ord-bb792770b2604df0a163e5f61dddc4f3
Source dataset
uspto-grants-1989_12
Patent number
US04888043

Reaction notes

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