Diethyl Ether → Estra-1,3,5(10),16-tetraen-3-ol

HRID 1264467Notes

Reaction equation

HRID 1264467 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[O:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.CCO[CH2:14][CH3:15]>C(COC)OC>[CH3:4][C@:3]12[CH2:15][CH2:14][C@H:4]3[C@@H:3]([CH2:4][CH2:7][C:8]4[CH:9]=[C:10]([OH:6])[CH:1]=[CH:2][C:3]=43)[C@@H:2]1[CH2:1][CH:1]=[CH:2]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 101988Estra-1,3,5(10),16-tetraen-3-ol

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Estra-1,3,5(10),16-tetraen-3-ol, for example, may be prepared from estrone (estra-1,3,5(10)-trien-3-ol-17-one) by reacting estrone with an appropriate amount of p-toluenesulfonylhydrazide in a polar solvent such as dry methanol or ethanol under reflux to form the corresponding estrone p-toluenesulfonylhydrazone. The estrone p-toluenesulfonylhydrazone is then reacted with n-butyl lithium in an inert aprotic solvent such as dry tetrahydrofuran, ether, dimethoxyethane or the like to give estra-1,3,5(10),16-tetraen-3-ol.

Sources & evidence

ORD record
ord-e40a7146e55c4a30bb5920e7d43fbf8f
Source dataset
uspto-grants-2003_04
Patent number
US06544971B1

Reaction notes

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