Methanol → HCID 14794005, Verbindung

HRID 1088017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088017
[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 (CDC13)δ1.2(s,6H), 1.3(t,3H), 3.2(s,3H), 3.7(m,1H), 4.2m,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-f6c2f0d5cf6a4896a99eb28cbd9926f3
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960946

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