4-Iodophenol → 5-[(4-Iodophenoxy)methyl]bicyclo[2.2.1]hept-2-ene

HRID 7328

Reaktionsgleichung

Reaktionsgleichung von HRID 7328
CCOC(/N=N/C(OCC)=O)=O.[CH:13]12[CH2:19][CH:16]([CH:17]=[CH:18]1)[CH2:15][CH:14]2[CH2:20][OH:21].[I:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[I:22][C:23]1[CH:28]=[CH:27][C:26]([O:21][CH2:20][CH:14]2[CH2:15][CH:16]3[CH2:19][CH:13]2[CH:18]=[CH:17]3)=[CH:25][CH:24]=1

Komponenten

6

Edukt 4

HCID 108944-IodophenolHCID 11776TriphenylphosphineHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanolHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 219893005-[(4-Iodophenoxy)methyl]bicyclo[2.2.1]hept-2-eneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethylazodicarboxylate (8.7 g) was added dropwise to a solution of 5-norbornene-2-methanol (6.2 g, 0.05 mol), 4-iodophenol (11.0 g, 0.05 mol) and triphenylphosphine (13.1 g, 0.05 mol) in 100 mL of anhydrous tetrahydrofuran. After completion of the addition, the resulting solution was stirred for 18 h at room temperature. The solvent was removed under reduced pressure and the oily residue was extracted three times with hot hexane. Combined hexane extracts were evaporated under reduced pressure to give 8 (15.0 g, 97%) as a colorless oil.

Aufarbeitung

  1. additionAfter completion of the addition
  2. customThe solvent was removed under reduced pressure
  3. extractionthe oily residue was extracted three times with hot hexane
  4. customCombined hexane extracts were evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fe246bcbccfc45eab97f443429b20fe3
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087267B2

Verknüpfte Notizen

Wird geladen…