Ammonia → HCID 68863993, Verbindung

HRID 1986615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986615
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]21[O:16][CH2:15][CH2:14][O:13]2.[NH3:17].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.C(Cl)Cl.O=[Mn]=O>[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:17])=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]21[O:16][CH2:15][CH2:14][O:13]2

Komponenten

7

Edukt 3

HCID 222AmmoniaHCID 24083Sulfuric acid magnesium salt (1:1)HCID 57722497HCID 57722497, Verbindung

Produkt 1

HCID 68863993HCID 68863993, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14801Manganese dioxideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the literature procedure of Lai, G. et al. (Synleft, 2001, 230-231), a stirred solution of 3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-6′-carbaldehyde (440 mg, 2.0 mmol) in THF (2 mL) was charged with NH3 (2M solution in isopropanol, 15 mL, 30 mmol, 15 eq) and anhydrous MgSO4 (3.64 g, 30 mmol, 15 eq). After 1 hour, MnO2 (Aldrich, 85%, 3.1 g, 30 mmol, 15 eq) was added in small portions and the resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was diluted with CH2Cl2 (40 mL) and filtered through Celite. The filtrate was concentrated in vacuo to give 0.42 g (100%) of 3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-6′-carbonitrile as a brown oil. 1H NMR (300 MHz, CDCl3): δ 7.42 (s, 1H), 7.40 (d, 1H, J=8.0 Hz), 7.12 (d, 1H, J=8.0 Hz), 4.03 (s, 4H), 3.02 (s, 2H), 3.00 (t, 2H, J=6.9 Hz), 1.96 (t, 2H, J=6.9 Hz). The material was sufficiently pure and it was used in the next step without further purification.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-843e29e1ac88451182f4212397eec8f0
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550467B2

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