Triphenylphosphine → 5-(3,4-Dichloro-benzylsulfanylmethyl)-6-((1S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 496443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496443
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][S:6][CH2:7][C:8]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][C:13]2=[O:19].[N:24]1([CH2:29][C@@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)O)[CH:28]=[CH:27][N:26]=[CH:25]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][S:6][CH2:7][C:8]1[C:17]([O:18][C@@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][C:13]2=[O:19]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 707108(R)-2-Imidazol-1-yl-1-phenyl-ethanolHCID 223246835-(3,4-Dichloro-benzylsulfanylmethyl)-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 697357885-(3,4-Dichloro-benzylsulfanylmethyl)-6-((1S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-oneAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-(3,4-Dichloro-benzylsulfanylmethyl)-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (256 mg, 0.69 mmol), (R)-2-imidazol-1-yl-1-phenyl-ethanol (144 mg, 0.75 mmol), and triphenylphosphine resin (1.46 g, loading 1.41 mmol/g) were combined in dry tetrahydrofuran (10 mL) and treated with diisopropyl azodicarboxylate (271 μL, 2.0 mmol). The resulting orange-brown heterogeneous mixture was allowed to stir at ambient temperature overnight. The spent triphenylphosphine resin was removed by filtration, washing sequentially with ethyl acetate, methanol, and chloroform. The filtrate was concentrated in vacuo and the crude material was purified by silica gel chromatography (hexanes/ethyl acetate/triethylamine 28:70:2) to give 280 mg (75%) of the desired product as a colorless solid: (LC-MS, APCI) m/z 553/555 [M+H]+.

Aufarbeitung

  1. customThe spent triphenylphosphine resin was removed by filtration
  2. washwashing sequentially with ethyl acetate, methanol, and chloroform
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe crude material was purified by silica gel chromatography (hexanes/ethyl acetate/triethylamine 28:70:2)

Quellen und Nachweise

ORD-Eintrag
ord-527bd0b7ee2148b38f782a3480ec09a4
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943183B2

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