HCID 54103955, compound → HCID 54537119, compound

HRID 1077156Notes

Reaction equation

HRID 1077156 reaction equation
[CH: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]2=[O:23])([CH3:3])[CH3:2]>O1CCOCC1.[Ni].[H][H]>[CH: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]2=[O:23])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 54103955HCID 54103955, compound

Product 1

HCID 54537119HCID 54537119, compoundYield 59.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 312751,4-DioxaneSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Shake 13β-isopropyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one (2 g) in dioxan (50 cc) with a freshly prepared but moderately active Raney nickel catalyst (ca. 0.5 g) in hydrogen at atmospheric pressure. When, after several hours the theoretical amount of hydrogen for half-hydrogenation (160 cc) has been absorbed, filter off the nickel catalyst and remove the solvent by evaporation. Crystallize the residual gum from methanol to obtain the title product (1.2 g), m.p. 85°-100°C; ultraviolet absorption peak at 280 mμ (ε11,800).

Workup

  1. customWhen, after several hours the theoretical amount of hydrogen for half-hydrogenation (160 cc) has been absorbed
  2. filtrationfilter off the nickel catalyst
  3. customremove the solvent
  4. customby evaporation
  5. customCrystallize the residual gum from methanol

Sources & evidence

ORD record
ord-b6cbb23f64254d1996f73f028b872776
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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