Water → HCID 14352792, compound

HRID 1576355Notes

Reaction equation

HRID 1576355 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@:19]3(O)[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:24])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].O>C(O)(=O)C>[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH:18]=3)([CH3:16])[C:14](=[O:24])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 15730353HCID 15730353, compound

Product 1

HCID 14352792HCID 14352792, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Acetoxy-9α-hydroxyoestra-1,3,5(10)-trien-17-one (100 mg) was reacted with ceric ammonium nitrate (0.33 g) in 90% aqueous acetic acid (50 ml) for 1 hour. The mixture was poured into water and extracted with ether to yield title compound (30%) m.p. 188°-190° and also 3-acetoxyoestra-1,3,5(10),9(11)-tetraen-17-one (30%) arising from acid dehydration of the 9α-hydroxy starting material and indicating that the starting material for the ceric oxidation is in fact the Δ9(11) compound formed in situ.

Workup

  1. extractionextracted with ether

Sources & evidence

ORD record
ord-35815cfc9d9b4b79b2fdeeba5fb93166
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

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