Potassium tert-butoxide → 1-Ethynyladamantane

HRID 231927

Reaktionsgleichung

Reaktionsgleichung von HRID 231927
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+]>C(O)COCCOCCO>[C:1]([C:2]12[CH2:5][CH:3]3[CH2:1][CH:2]([CH2:5][CH:1]([CH2:2]3)[CH2:3]1)[CH2:3]2)#[CH:5]

Komponenten

3

Edukt 1

HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 5947811-Ethynyladamantane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8172Triethylene GlycolLösungsmittel

Versuchsvorschrift

The Stetter and Goebel reference, also cited above, discloses the synthesis of 1-ethynyladamantane from 1-bromoadamantane in good yield. We repeated that procedure with minor modifications by reacting 1-bromoadamantane with vinyl bromide in the presence of aluminum bromide to give the 2,2-dibromoethyl derivative, then dehydrobrominating that derivative in situ with potassium t-butoxide in triethylene glycol to give 1-ethynyladamantane in 60% overall yield.

Quellen und Nachweise

ORD-Eintrag
ord-60d1d5d460fa420fad74efae9ba9ab7d
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849565

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