Toluene → HCID 66926552, Verbindung

HRID 2404214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404214
[CH2:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH3:12][O:13][C:14]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21](O)[CH:22]=2)[CH:17]=1)=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH2:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:21]3[CH:22]=[C:23]4[C:18](=[CH:19][CH:20]=3)[CH:17]=[C:16]([C:14]([O:13][CH3:12])=[O:15])[CH:25]=[CH:24]4)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 390995Methyl 6-hydroxy-2-naphthoateHCID 56962207Spiro[4.5]decan-8-ol

Produkt 1

HCID 66926552HCID 66926552, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The mixture of spiro[4.5]decan-8-ol (0.915 g, 0.00593 mol), 6-hydroxy-naphthalene-2-carboxylic acid methyl ester (1.00 g, 0.00494 mol) and triphenylphosphine (1.56 g, 0.00593 mol) in toluene (10 mL, 0.1 mol) was heated to reflux, and diisopropyl azodicarboxylate (1.17 mL, 0.00593 mol) was added dropwise and was stirred and refluxed for 6 hours. The mixture was taken up into DCM and subjected to chromatography purification with EtOAc/hexane (0:100 to 40:60) to give product as a white solid (1.02 g, 61%). LCMS Rt=2.58 min, m/z=339.34, (M+1, 100%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturerefluxed for 6 hours
  4. customsubjected to chromatography purification with EtOAc/hexane (0:100 to 40:60)

Quellen und Nachweise

ORD-Eintrag
ord-4ed8844f67a94cd4a1619f8ba8257d19
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802659B2

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