HCID 54050571, compound → HCID 54358169, compound

HRID 648781Notes

Reaction equation

HRID 648781 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3]1>C(OCC)(=O)C.[Pd]>[O:1]=[C:2]1[CH2:7][CH2:6][C@@H:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@@H:4]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 54050571HCID 54050571, compound

Product 1

HCID 54358169HCID 54358169, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of the ethylene ketal of ethyl (4-keto-2-phenylcyclohex-1-enyl)-acetate (7.0 g.) in ethyl acetate (70 ml.) was hydrogenated at atmospheric pressure over a 5% w/w palladium-on-charcoal catalyst (0.7 g.) for 16 hours. The mixture was filtered through diatomaceous earth and the filtrate was evaporated. The residue was purified by flash chromatography on silica, eluting with ether/hexane (4:6 v/v), to give the ethylene ketal of ethyl (4-keto-2-phenyl-cis-cyclohexyl)acetate (6.2 g.), as a colourless solid, m.p. 83°-86° C.; NMR (CDCl3): 3.29 (1H, d of t, Jaa=13 Hz, Jae=3 Hz, Jae=3 Hz, cis-Ph.CH); mass spectrum: m/e 304.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residue was purified by flash chromatography on silica
  4. washeluting with ether/hexane (4:6 v/v)

Sources & evidence

ORD record
ord-0330ca75f0814a4f8df28f0115a48d9b
Source dataset
uspto-grants-1988_04
Patent number
US04736057

Reaction notes

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