HCID 22789123, compound → HCID 68147558, compound

HRID 1606290Notes

Reaction equation

HRID 1606290 reaction equation
[CH3:1][O:2][C:3]1[C:20]2[C:19]3[CH2:18][CH2:17][C@@:15]4([CH3:16])[C:11](=[CH:12][CH2:13][C:14]4=[O:21])[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=1>[Pd].C([O-])([O-])=O.[Ca+2].C1COCC1>[CH3:1][O:2][C:3]1[C:20]2[C@@H:19]3[C@@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:21])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=1

Participants

4

Reactant 1

HCID 22789123HCID 22789123, compound

Product 1

HCID 68147558HCID 68147558, compound

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In the presence of 0.15 g. of palladium/CaCO3 (5%), 0.3 g. of rac.-1,3-dimethoxy-1,3,5(10),8,14-estrapentaen-17-one in 50 ml. of THF is hydrogenated within 17 hours at room temperature and under a hydrogen pressure of 50 atmosphere gauge. Then, the mixture is filtered off from the catalyst, the filtrate is concentrated by evaporation, and the residue is recrystallized from isopropyl ether, thus obtaining 40 mg. of final product, m.p. 158°-160°C.

Workup

  1. filtrationThen, the mixture is filtered off from the catalyst
  2. concentrationthe filtrate is concentrated by evaporation
  3. customthe residue is recrystallized from isopropyl ether
  4. customthus obtaining 40 mg

Sources & evidence

ORD record
ord-3b5066098a4a4ae086fdc54ca234715c
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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