Acetaldehyde → HCID 178477243, Verbindung

HRID 868490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 868490
[Cl-].[Cl-].[CH:3]([O:6][Ti+2:7][O:8][CH:9]([CH3:11])[CH3:10])([CH3:5])[CH3:4].[CH:12](=[O:14])[CH3:13].C1C[O:18][CH2:17][CH2:16]1>>[CH:3]([O:6][Ti:7]([O:8][CH:9]([CH3:11])[CH3:10])([O:18][CH:17]=[CH2:16])[O:14][CH:12]=[CH2:13])([CH3:5])[CH3:4]

Komponenten

4

Edukt 3

HCID 177AcetaldehydeHCID 8028Tetrahydrofuran2×HCID 178460659HCID 178460659, Verbindung

Produkt 1

HCID 178477243HCID 178477243, Verbindung

Versuchsvorschrift

Diisopropoxytitanium dichloride (0.262 g, 1.10 mmol) was dissolved in 20 ml of THF (dry, nitrogen atmosphere) in a 100 ml Schlenk flask. This solution was cooled to -78° C. at which point the lithium enolate of acetaldehyde, CH2 =CHOLi, in THF solution (2.20 mmol) was added to the stirred solution via syringe. This solution was allowed to warm to room temperature. After two hours of stirring, the solvent was evaporated by trap-to-trap distillation, leaving a yellow solid. This solid was extracted with pentane yielding a yellow pentane-soluble solid (crude yield 0.19 g, 70%). 1H NRM (CDCl3) δ 1.19 (d, J=6.4 Hz, 6.7H, CH--(CH3)2), 3.10 (d, J=28 Hz, 1H, OCH=CH2), 3.62 (s, 1H, OCH=CH2), 4.00 (sept, J=6.45 Hz, 1H, CH--(CH3)2), 6.55 (d, J=10.3 Hz, 1H, OCH=CH2), 7.01 (d, J=19.7, 1H, OCH=CH2).

Aufarbeitung

  1. customthe solvent was evaporated by trap-to-trap
  2. distillationdistillation
  3. customleaving a yellow solid
  4. extractionThis solid was extracted with pentane yielding a yellow pentane-soluble solid (crude yield 0.19 g, 70%)

Quellen und Nachweise

ORD-Eintrag
ord-4f35ce40b0c04908b6f0321fd4497b53
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04780337

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