Hydrazine hydrate (1:1) → HCID 89375802, Verbindung

HRID 1752257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752257
[CH:1]([C:3]1[O:8][CH2:7][CH2:6][CH2:5][C:4]=1[C:9]([O:11]CC)=O)=O.O.[NH2:15][NH2:16]>CO>[O:8]1[C:3]2[CH:1]=[N:15][NH:16][C:9](=[O:11])[C:4]=2[CH2:5][CH2:6][CH2:7]1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 89375787HCID 89375787, Verbindung

Produkt 1

HCID 89375802HCID 89375802, VerbindungAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a stirred 0° C. mixture of ethyl 6-formyl-3,4-dihydro-2H-pyran-5-carboxylate (1.705 g, 9.26 mmol) in methanol (80 mL) was added very quickly 35% hydrazine hydrate (0.311 g, 9.72 mmol). After 20 minutes, the solvent was removed under reduced pressure, and the residue was treated with acetic acid (70 mL) and water (7 mL) and stirred at 110° C. for 20 minutes. The solvents were removed in vacuo. The crude residue was eluted by silica gel chromatography with a 0 to 25% gradient of methanol/dichloromethane to afford the title compound (1.384 g) as a light yellow solid in better than 90% purity. MS (ESI) [m/e, (M+H)+]=153.2. 1H NMR (400 MHz, chloroform-d) δ ppm 10.56 (br s, 1H), 7.53 (s, 1H), 4.17-4.35 (m, 2H), 2.57 (t, J=6.57 Hz, 2H), 1.99-2.08 (m, 2H).

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. additionthe residue was treated with acetic acid (70 mL) and water (7 mL)
  3. customThe solvents were removed in vacuo
  4. washThe crude residue was eluted by silica gel chromatography with a 0 to 25% gradient of methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-f7d82551f17048febafc97110da45c48
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163003B2

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