HCID 54013930, compound → HCID 53837423, compound

HRID 1077159Notes

Reaction equation

HRID 1077159 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([OH:20])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C:7]1=[CH:6][CH2:5][C:4]2=[O:21])[CH3:2]>C1C=CC=CC=1.C>[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([OH:20])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:21])[CH3:2]

Participants

4

Reactant 1

HCID 54013930HCID 54013930, compound

Product 1

HCID 53837423HCID 53837423, compound

Reagents, catalysts & solvents 2

HCID 297MethaneCatalystHCID 241BenzeneSolvent

Procedure

Hydrogenate 13β-ethyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17-one (0.5 g.) in benzene (25 cc.) at atmospheric pressure using a 10% palladized charcoal catalyst (0.025 g.). After the absorption of 1.1 molar equivalents of hydrogen, hydrogenation becomes very slow; remove the catalyst by filtration and evaporate the filtrate to obtain the title product which crystallizes from methanol in colorless plates (0.35 g.), m.p. 235°-9°; ultra-violet absorption peak at 280.5 mμ (ε15,500).

Workup

  1. customAfter the absorption of 1.1 molar equivalents of hydrogen, hydrogenation
  2. customremove the catalyst
  3. filtrationby filtration
  4. customevaporate the filtrate

Sources & evidence

ORD record
ord-d983c9c4936443a782294adfddc3f10b
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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