HCID 54083457, compound → HCID 53869552, compound

HRID 1414985Notes

Reaction equation

HRID 1414985 reaction equation
[CH2:1]([C@:4]12[CH2:12][CH2:11][C:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C:9]=3[C:8]1=[CH:7][CH2:6][C:5]12[O:26][CH2:25][CH2:24][O:23]1)[CH2:2][CH3:3].[H][H]>C1C=CC=CC=1.[Pd]>[CH2:1]([C@:4]12[CH2:12][CH2:11][C:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C:9]=3[C@@H:8]1[CH2:7][CH2:6][C:5]12[O:23][CH2:24][CH2:25][O:26]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 54083457HCID 54083457, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53869552HCID 53869552, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

Shake 13β-propyl-3-methoxy-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene (2.5 g.) in benzene (80 cc.) with hydrogen at atmospheric pressure in the presence of a 2% palladium on calcium carbonate catalyst (0.9 g.); hydrogen uptake ceases after the requisite amount (161 cc.) for monohydrogenation has been absorbed. Filter and evaporate to obtain a gum, which one crystallizes from ethanol to obtain the title product (1.8 g.), m.p. 119°-120°; ultraviolet absorption peak at 278 mμ (ε15,300).

Workup

  1. customhydrogen uptake ceases after the requisite amount (161 cc.) for monohydrogenation has been absorbed
  2. filtrationFilter
  3. customevaporate
  4. customto obtain a gum, which one
  5. customcrystallizes from ethanol

Sources & evidence

ORD record
ord-8ae572074a68442fbb875cb3d895b47f
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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