HCID 70544774, compound → HCID 86738407, compound

HRID 1156046Notes

Reaction equation

HRID 1156046 reaction equation
[CH:1](=[C:3]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]2([CH2:6][CH3:7])[C:4]1=[O:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)[CH3:2]>C(O)C.[Pd]>[CH2:1]([C@H:3]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]2([CH2:6][CH3:7])[C:4]1=[O:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)[CH3:2]

Participants

4

Reactant 1

HCID 70544774HCID 70544774, compound

Product 1

HCID 86738407HCID 86738407, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.3 g of 16-ethylidene-3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one in 180 ml of ethanol is hydrogenated, after adding 130 mg of 10% palladium charcoal, at room temperature and normal pressure. After absorbing 115 ml of hydrogen the reaction product is filtered off from the catalyst and the filtrate concentrated. Crystallization from methanol yields 1.3 g of 16β-ethyl-3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one, m.p. 101°-102° C.

Workup

  1. customat room temperature
  2. customAfter absorbing 115 ml of hydrogen the reaction product
  3. filtrationis filtered off from the catalyst
  4. concentrationthe filtrate concentrated
  5. customCrystallization from methanol

Sources & evidence

ORD record
ord-5315c6a7344c499db953459c3002437f
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

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