Triphenylphosphine → HCID 68576812, Verbindung

HRID 273059Notizen

Reaktionsgleichung

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:16]([N:29]1[CH2:32][CH:31]([CH2:33]O)[CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[C:17]1([CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:29]2[CH2:32][CH:31]([CH2:33][O:1][C:2]3[CH:7]=[CH:6][C:5]([C:8]4([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)=[CH:4][CH:3]=3)[CH2:30]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

Edukt 4

HCID 11776Triphenylphosphine

HCID 2758715(1-Benzhydrylazetidin-3-yl)methanol

HCID 5363146Diisopropyl azodicarboxylate

HCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

Produkt 1

HCID 68576812HCID 68576812, VerbindungAusbeute 41 %

Versuchsvorschrift

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (6.18 g, 30.4 mmol), (1-benzhydryl-azetidin-3-yl)-methanol (7 g, 28 mmol), PPh3 (8 g, 30.4 mmol), and DIAD (69 mL, 30.4 mmol), were reacted together similarly to general procedure C. The crude material was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate:diethylamine (50:45:5 to 0:95:5) to provide the title compound (5.03 g, 41%) as a yellow solid. LRMS APCI+ m/z 439 [MH]+.

Aufarbeitung

customThe crude material was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate:diethylamine (50:45:5 to 0:95:5)

Quellen und Nachweise

ORD-Eintrag: ord-0d883d44d0d948f49b462a0f42631ff9
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07456164B2

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