Propanal → Hept-3-yne-2,5-diol
Reaktionsgleichung
[CH:1]#[C:2][CH:3]([OH:5])[CH3:4].[CH:6](=[O:9])[CH2:7]C.[CH2:10]([Mg]Br)C>>[CH3:7][CH:6]([OH:9])[C:1]#[C:2][CH:3]([OH:5])[CH2:4][CH3:10]Komponenten
4
Versuchsvorschrift
0.5 mole of 1-butyn-3-ol was coupled with 0.5 mole of propionaldehyde under the influence of ethylmagnesium bromide according to Bull.Soc.Chim.(Fr.) 425 (1956) and 3-heptyne-2,5-diol (b.p. 109°-110° C at 2 mm Hg) was obtained in 64% yield. The alkyne diol was esterified with p-toluene sulfonylchloride as described in Example 1A and 3-heptyne-2,5-ditosylate (m.p. 69.5°-70.5° C) was obtained in 76% yield. The alkyne ditosylate was oxidised with aqueous potassium permanganate as described in Example 2A, at a temperature of 5° C and heptane-3,4-dione-2,5-ditosylate was obtained in 55% yield; m.p. 120°-121.5° C (from tetrachloromethane).
Quellen und Nachweise
- ORD-Eintrag
- ord-e610302cd64c4f428314c2186bc8599e
- Quelldatensatz
- uspto-grants-1978_03
- Patentnummer
- US04080367
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