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

HRID 404255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404255
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-b5afb2c1b9e847f791564d107c9f3382
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748469B2

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