16-Ethylidene-3-methoxy-1,3,5(10)-estratrien-17-one → 16beta-Ethyl-3-methoxy-1,3,5(10)-estratrien-17-one

HRID 1154782Notes

Reaction equation

HRID 1154782 reaction equation
[CH:1](=[C:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C:4]1=[O:23])[C:17]1[CH:16]=[CH:15][C:14]([O:21][CH3:22])=[CH:13][C:12]=1[CH2:11][CH2:10]3)[CH3:2]>[Pd].C(O)C>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C:4]1=[O:23])[C:17]1[CH:16]=[CH:15][C:14]([O:21][CH3:22])=[CH:13][C:12]=1[CH2:11][CH2:10]3)[CH3:2]

Participants

4

Reactant 1

HCID 5422152916-Ethylidene-3-methoxy-1,3,5(10)-estratrien-17-one

Product 1

HCID 2281835316beta-Ethyl-3-methoxy-1,3,5(10)-estratrien-17-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2.0 g. of 16-ethylidene-3-methoxy-1,3,5(10)-estratrien-17-one in 80 ml. of ethanol is combined with 200 mg. of 10% palladium-charcoal and hydrogenated for 60 minutes at room temperature under normal pressure. After removing the catalyst by filtration and concentration of the reaction product, 2.0 g. of 16β-ethyl-3-methoxy-1,3,5(10)-estratrien-17-one is obtained, m.p. 93°-94° C.

Workup

  1. additionA suspension of 2.0 g
  2. customAfter removing the catalyst
  3. filtrationby filtration and concentration of the reaction product, 2.0 g

Sources & evidence

ORD record
ord-55f2704828c44f909ce30d3b8710b80c
Source dataset
uspto-grants-1981_11
Patent number
US04298538

Reaction notes

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