HCID 54091434, compound → HCID 53866954, compound

HRID 1414974Notes

Reaction equation

HRID 1414974 reaction equation
[CH2:1]([C@:5]12[CH2:13][CH2:12][C:11]3[C:14]4[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[CH:18][C:19]=4[CH2:20][CH2:21][C:10]=3[C:9]1=[CH:8][CH2:7][C:6]2=[O:24])[CH:2]([CH3:4])[CH3:3].[H][H]>[Pd].C1C=CC=CC=1>[CH2:1]([C@:5]12[CH2:13][CH2:12][C:11]3[C:14]4[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[CH:18][C:19]=4[CH2:20][CH2:21][C:10]=3[C@@H:9]1[CH2:8][CH2:7][C:6]2=[O:24])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 54091434HCID 54091434, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53866954HCID 53866954, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent2×

Procedure

To a pre-reduced suspension of 2% palladium on calcium carbonate catalyst (7.0 g) in benzene (30 cc) add a solution of 13β-isobutyl-3-methoxygona-1,3,5(10), 8,14-pentaen-17-one (20.0 g) in benzene (500 cc) and hydrogenate the mixture at atmospheric pressure until one mole equivalent of hydrogen is consumed. After the catalyst is removed by filtration, evaporate the solvent to obtain a gum which on crystallization from ethanol affords the title product (17.1 g.; 71%), m.p. 117°-119°; ultraviolet absorption peak at 278 mμ (ε14,560).

Workup

  1. customis consumed
  2. customAfter the catalyst is removed by filtration
  3. customevaporate the solvent
  4. customto obtain a gum which
  5. customon crystallization from ethanol

Sources & evidence

ORD record
ord-fdece3c15a6b4b9e81575c8ce76d84dd
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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