Acetic Acid → ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

HRID 1748880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748880
C1(C(=[N:14][CH:15]([CH2:21][CH:22]=[C:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.O.C(O)(=O)C>C1COCC1>[NH2:14][CH:15]([CH2:21][CH:22]=[C:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 962WaterHCID 58313138ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

Produkt 1

HCID 58313060ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoateAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate (162) (6.8 g, 18.0 mmol) in THF (30 mL) was added water (30 mL) and glacial acetic acid (20 mL) and the reaction stirred at room temperature for 2.5 h. The reaction was concentrated in vacuo and the residue dissolved in 0.1 N HCl. It was extracted twice with ethyl acetate and the organic layer was discarded. To the aqueous layer was added solid potassium carbonate until the solution gave blue pH paper. The aqueous layer was extracted with 15% isopropanol/dichloromethane (3×) and the organic layer dried over sodium sulfate and concentrated in vacuo to afford the title compound as a clear oil (3.05 g, 79% yield).

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in 0.1 N HCl
  3. extractionIt was extracted twice with ethyl acetate
  4. additionTo the aqueous layer was added solid potassium carbonate until the solution
  5. customgave blue pH paper
  6. extractionThe aqueous layer was extracted with 15% isopropanol/dichloromethane (3×)
  7. dry with materialthe organic layer dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-20f5fe714e414f7c98f92ce1ae31fd27
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150587B2

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