HCID 68148900, compound → HCID 88848295, compound

HRID 1606274Notes

Reaction equation

HRID 1606274 reaction equation
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[CH:16]=[CH:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:23][C:24](=[O:26])[CH3:25])[CH:6]=1)(=[O:3])[CH3:2].CC[O:29]CC.C1C=C(C(O)=O)C(C(OO)=O)=CC=1>CCOCC>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]3[O:29][C@@H:15]3[CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:23][C:24](=[O:26])[CH3:25])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 68148900HCID 68148900, compoundHCID 131710144HCID 131710144, compound

Product 1

HCID 88848295HCID 88848295, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 350 mg. of 1,3-diacetoxy-8α-estra-1,3,5(10),16-tetraene in 15 ml. of ether is combined with 7 ml. of a 12% strength ether - monoperphthalic acid solution. After allowing the mixture to stand at room temperature for 7.5 hours, the mixture is worked up, yielding 1,3-diacetoxy-16α,17α-epoxy-8α-estra-1,3,5(10)-triene which, in the form of the crude product, is heated to the boiling point with 30 ml. of glacial acetic acid for 2-3 hours. After concentration under vacuum, the residue is heated, for purposes of esterification, with 2 ml. of pyridine and 2 ml. of acetic anhydride for 1.5 hours on a steam bath under N2. After the mixture has been introduced into ice water, it is taken up in methylene chloride and worked up, thus producing, after purification by chromatography on SiO2, 1,3,16β,17α-tetraacetoxy-8α-estra-1,3,5(10)-triene.

Sources & evidence

ORD record
ord-82f62f0ff9de4536be853f3e681baeae
Source dataset
uspto-grants-1976_04
Patent number
US03951958

Reaction notes

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