Triphenylphosphine → 3-[[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

HRID 1161096

Reaktionsgleichung

Reaktionsgleichung von HRID 1161096
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:17]([OH:26])=[C:18]([C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][C:21]=1[OH:22].O[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([O:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][O:46]2)[C:36]2[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=2)[C:39]#[N:40])=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:23]([C:18]1[CH:19]=[CH:20][C:21]([O:22][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([CH:35]([O:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][O:46]3)[C:36]3[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=3)[C:39]#[N:40])=[CH:33][CH:34]=2)=[C:16]([Cl:15])[C:17]=1[OH:26])(=[O:25])[CH3:24]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 574382941-(3-Chloro-2,4-dihydroxy-phenyl)ethanoneHCID 574382993-[(4-Hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

Produkt 1

HCID 578844993-[[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrileAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add diisopropylazodicarboxylate (DIAD, 5.418 g, 26.80 mmol) to a solution of 1-(3-chloro-2,4-dihydroxy-phenyl)ethanone (5.000 g, 26.80 mmol), 3-[(4-hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (8.666 g, 26.80 mmol), and triphenylphosphine (7.028 g, 26.80 mmol) in tetrahydrofuran (0.200M) at 0° C. Stir for 2 hours while warming to room temperature. Add silica gel and evaporate solvent. Chromatograph with Biotage Flash 75, eluting with 50-90% ethyl acetate/hexanes to afford the title compound as a white solid (13.00 g, 26.42 mmol, 98%): MS (m/z): 490 (M−H).

Aufarbeitung

  1. customAdd silica gel and evaporate solvent
  2. washChromatograph with Biotage Flash 75, eluting with 50-90% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-224f780b7dfb420aab9a31e7d8c7ef2f
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816523B2

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