Triethylamine → Diethyl 4-(triphenylen-2-yl)benzylphosphonate

HRID 871818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871818
O1[CH:5]2[C:6]3[C:7]4[C:12]([C:13]5[C:18]([C:19]=3[CH:2]1[CH:3]=[CH:4]2)=[CH:17][CH:16]=[CH:15][CH:14]=5)=[CH:11][CH:10]=[CH:9][CH:8]=4.I[C:21]1[CH:35]=[CH:34][C:24]([CH2:25][P:26](=[O:33])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[CH:23][CH:22]=1.IC1C=C(C=CC=1)CP(=O)(OCC)OCC.C(N(CC)CC)C>[Zn].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH:5]1[C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]=2[CH:2]=[CH:3][C:4]=1[C:21]1[CH:35]=[CH:34][C:24]([CH2:25][P:26](=[O:33])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[CH:23][CH:22]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 126679791,4-Dihydro-1,4-epoxytriphenyleneHCID 15166405Diethyl ((4-iodophenyl)methyl)phosphonateHCID 58999960Diethyl 3-iodobenzylphosphonate

Produkt 1

HCID 86675394Diethyl 4-(triphenylen-2-yl)benzylphosphonateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Compound A (760 mg, 3.11 mmol), zinc (1.85 g, 28.2 mmol), and PdCl2(PPh3)2 (198 mg, 0.28 mmol) were charged in a two-necked bottle. The bottle was then vacuumed and purged with nitrogen, and dried toluene (30 mL), diethyl 4-iodobenzylphosphonate (0.65 mL, 2.82 mmol) or diethyl 3-iodobenzylphosphonate, and triethyl amine (3.91 mL, 28.2 mmol) were added to the bottle. The mixture in the bottle was heated to 110° C. for reaction for 48 hours, and the resulting was filtered to remove metal. The filtrate was condensed to remove the solvent, and then purified by column chromatography (ethyl acetate/hexanes=½) to obtain E (0.90 g, yield=70%) as white solid.

Aufarbeitung

  1. additionwere added to the bottle
  2. filtrationthe resulting was filtered
  3. customto remove metal
  4. customcondensed
  5. customto remove the solvent
  6. custompurified by column chromatography (ethyl acetate/hexanes=½)
  7. customto obtain E (0.90 g, yield=70%) as white solid

Quellen und Nachweise

ORD-Eintrag
ord-d0772baeb8574a958c1b3e9da117922b
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08974920B2

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