Hydrochloric Acid → 1-Phenoxy-4-trimethylsilylbut-3-yn-2-ol
Reaktionsgleichung
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[O:12]([CH2:19][CH:20]=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C1COCC1.CCCCCC.CCOCC.CCCCCC>[O:12]([CH2:19][CH:20]([OH:21])[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
To 7.2 g of trimethylsilylacetylene dissolved in 110 ml of THF and cooled to -20° C. was added 46.2 ml of 1.55M n-butyl lithium in hexane. The mixture was allowed to come to room temperature for 15 minutes, recooled to -20° C., and treated dropwise with 5.3 g of phenoxyacetaldehyde (II) in THF. After the addition was complete, the reaction mixture was stirred at 0° C. for 4 hours. The reaction mixture was then poured into a mixture of ether:hexane (1:1) over 0.5N HCl and shaken. The organic layer was separated, washed 3 times with H2O, dried (Na2SO4), and evaporated to dryness. The residue was chromatographed on a column of silica gel that was eluted with 30% ethyl acetate in hexane to yield 3.8 g of 1-phenoxy-4-trimethylsilylbut-3-yn-2-ol (III).
Aufarbeitung
- customrecooled to -20° C.
- additionAfter the addition
- stirringshaken
- customThe organic layer was separated
- washwashed 3 times with H2O
- dry with materialdried (Na2SO4)
- customevaporated to dryness
- customThe residue was chromatographed on a column of silica gel that
- washwas eluted with 30% ethyl acetate in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-7fe5eddca4bb4adf902f4296a00c90fb
- Quelldatensatz
- uspto-grants-1987_08
- Patentnummer
- US04689419
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