HCID 68137148, compound → Estra-1,3,5(10),8-tetraen-17-one, 3-methoxy-

HRID 1576167Notes

Reaction equation

HRID 1576167 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH:10]=[CH:11][C:12]4=[O:21])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1.[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH2:10][CH2:11][C:12]4=[O:21])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 68137148HCID 68137148, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11055125Estra-1,3,5(10),8-tetraen-17-one, 3-methoxy-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.5 g. of 3-methoxy-14α-estra-1,3,5(10), 8,15-pentaen-17-one in 25 ml. of ethanol is reduced catalytically with 50 mg. of 5% palladium-on-charcoal until a molar equivalent of hydrogen is taken up. The catalyst is filtered off and the filtrate evaporated to dryness to yield the known 3-methoxyestra-1,3,5 (10),8-tetraen-17-one which can be converted into estrone methyl ether by procedures outlined in Chemistry & Industry (London), 1022 (1960) or into 19-nor-Δ4 -steroids using the procedure of, for example, U.S. Pat. No. 3,318,922.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-be0d6ad84d4143ff90c3f39bd1a59014
Source dataset
uspto-grants-1976_09
Patent number
US03979458

Reaction notes

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