HCID 136109361, compound → HCID 136006884, compound

HRID 979000Notes

Reaction equation

HRID 979000 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([CH:17]2[CH2:22][C:21](=[O:23])[C:20]([C:24](=[N:28][O:29][CH2:30][CH3:31])[CH2:25][CH2:26][CH3:27])=[C:19]([OH:32])[CH2:18]2)=[C:11]([CH3:33])[C:10]=1[CH3:34])C1C=CC=CC=1>[Pd].Cl.C(OCC)(=O)C>[CH2:30]([O:29][N:28]=[C:24]([C:20]1[C:19](=[O:32])[CH2:18][CH:17]([C:12]2[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]([OH:8])=[C:10]([CH3:34])[C:11]=2[CH3:33])[CH2:22][C:21]=1[OH:23])[CH2:25][CH2:26][CH3:27])[CH3:31]

Participants

5

Reactant 1

HCID 136109361HCID 136109361, compound

Product 1

HCID 136006884HCID 136006884, compoundYield 30.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on activated carbon (0.14 g), followed by concentrated hydrochloric acid (2 drops), were added to a solution of 5-(4-benzyloxy-2,3,5,6-tetramethylphenyl)-2-[1-(ethoxyimino)butyl]-3-hydroxycyclohex-2-en-1-one (see Example 37) (1.40 g; 3.0 mmole) in ethyl acetate (50 ml). The mixture was hydrogenated at atmospheric pressure for 2 hours, then filtered, washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent gave an oily residue, which was purified by column chromatography over silica gel (eluant dichloromethane) to give 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(4-hydroxy-2,3,5,6-tetramethylphenyl)cyclohex-2-en-1-one (0.34 g; 30.1%) as a colourless solid, mp 134° C.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent
  5. customgave an oily residue, which
  6. customwas purified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-3292ea938a434474adb4a63169f04be8
Source dataset
uspto-grants-1987_05
Patent number
US04666510

Reaction notes

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