Triphenylphosphine → 5,6-Dihydroimidazo[1,5-d][1,4]benzoxazepine

HRID 705425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705425
O[CH2:2][CH2:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:7][N:6]=[CH:5]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:7]1[N:6]=[CH:5][N:4]2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:2][CH2:3]2

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 582941362-(1-(2-hydroxyethyl)-1H-imidazol-5-yl)phenol

Produkt 1

HCID 582941105,6-Dihydroimidazo[1,5-d][1,4]benzoxazepineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(1-(2-hydroxyethyl)-1H-imidazol-5-yl)phenol (103.0 mg, 0.5 mmol) and PPh3 (157.0 mg, 0.6 mmol) in THF (4 mL) at 0° C., was added DEAD (0.22 mL, 40% solution in toluene, 0.75 mmol). The resulting yellow solution was allowed to warm to rt and stirred overnight. The solvent was removed under reduced pressure and the crude residue was purified by flash column chromatography on silica gel to afford the desired product in 84% yield. 1H NMR: 4.35-4.45 (m, 4H), 6.94-7.05 (m, 2H), 7.11-7.19 (m, 1H), 7.43 (d, 1H, J=0.8 Hz), 7.49 (s, 1H), 7.67 (dd, 1H, J=1.6, 8.0 Hz).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe crude residue was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-de3ff9238df1414bbe0ee4e3b4eacd48
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174942B2

Notizen zur Reaktion

Wird geladen…