6-Methylhepta-3,5-dien-2-one → 4,8-Dimethylnon-7-EN-1-YN-4-OL

HRID 231569

Reaktionsgleichung

Reaktionsgleichung von HRID 231569
[CH3:1][C:2]([CH3:9])=[CH:3][CH:4]=[CH:5][C:6](=[O:8])[CH3:7].[CH2:10]([Mg]Br)[C:11]#[CH:12]>>[CH3:7][C:6]([OH:8])([CH2:5][CH2:4][CH:3]=[C:2]([CH3:9])[CH3:1])[CH2:12][C:11]#[CH:10]

Komponenten

3

Edukt 2

HCID 279716-Methylhepta-3,5-dien-2-oneHCID 178455849HCID 178455849, Verbindung

Produkt 1

HCID 183594254,8-Dimethylnon-7-EN-1-YN-4-OL

Versuchsvorschrift

Reaction of this ketone with propargyl magnesium bromide provides 4,8-dimethyl-4-hydroxy non-7-ene-1-yne. This alcohol is protected with trimethylsilyl chloride and converted to trans vinyl tin derivative of 4,7-dimethyl-4-trimethylsiloxy-non-8-ene-1-yne which is converted to the corresponding prostaglandin by the methods described in U.S. Pat. Nos. 4,322,543 and 4,271,314 to provide methyl 7-[3α-hydroxy-2β-(4-hydroxy-4,8-dimethyl-1,5,7-trans,trans,trans-nonatrienyl-5-oxocyclopentane]-1α-hept-4-cis-enoate having the formula ##STR14##

Quellen und Nachweise

ORD-Eintrag
ord-c4f84816ead54c7e899b7f273a6dddde
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847293

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