Methanol → HCID 14794005, Verbindung

HRID 2247811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247811
[OH:1][C:2]1C(=O)O[CH:5]=[CH:6][CH:7]=1.[CH3:9][O:10][C:11]([CH3:22])([CH3:21])[CH2:12][CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].CO.[H][H]>C1(C)C=CC=CC=1.[Pd]>[C:16]([CH:15]1[CH:14]([CH2:13][CH2:12][C:11]([O:10][CH3:9])([CH3:21])[CH3:22])[CH2:5][CH2:6][CH2:7][C:2]1=[O:1])([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 681303-Hydroxy-2H-pyran-2-oneHCID 53765586HCID 53765586, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 14794005HCID 14794005, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3-Hydroxypyrone (obtained by the procedure of R. H. Wiley and C. H. Jorboe, J. Am. Chem. Soc.,78, 2398, (1956), 5.0 g, 0.045 mol) and ethyl 6-methoxy-6-methyl-2-heptenoate (8.9 g, 0.045 mol) were dissolved in toluene (15 mL) and heated in a sealed vessel for 7 hours at 200~C. After cooling 5% Pd/C (1.0 g) and methanol (50 mL) were added and the vessel was pressurized with hydrogen gas (200 psi). After stirring 20 hours the mixture was filtered and concentrated to the residue. The crude product decomposed on distillation. No further purification was attempted. NMR of crude material (CDCl3)δ 1.2(s,6H), 1.3(t,3H), 3.2(s,3H), 3.7(m,1H), 4.2(m,2H); IR (neat) 2600-3800, (broad band), 2990, 2950, 1740, 1720, 1680, 1650, 1620, 1470, 1390, 1370, 1220, 1090 cm-1.

Aufarbeitung

  1. customobtained by the procedure of R
  2. temperatureheated in a sealed vessel for 7 hours at 200~C
  3. additionwere added
  4. filtrationwas filtered
  5. concentrationconcentrated to the residue
  6. distillationThe crude product decomposed on distillation
  7. customNo further purification

Quellen und Nachweise

ORD-Eintrag
ord-fbc1acdd1dc94422a7edb6dc833774ae
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05037802

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