Triethyl Phosphate → Diethyl (2-bromo-1-oxoindan-4-yl)methylphosphonate

HRID 1870811

Reaktionsgleichung

Reaktionsgleichung von HRID 1870811
[O:1]=[C:2]1[C:10]2[C:5](=[C:6]([CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[Br:20]CC1C=CC=C2C=1CCC2=O.P(OCC)(OCC)(OCC)=O>C1(C)C(C)=CC=CC=1>[Br:20][CH:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:11][P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])[C:2]1=[O:1]

Komponenten

5

Edukt 3

HCID 6535Triethyl PhosphateHCID 186940504-(Bromomethyl)indan-1-oneHCID 18694052Diethyl 1-oxoindan-4-ylmethylphosphonate

Produkt 1

HCID 18694081Diethyl (2-bromo-1-oxoindan-4-yl)methylphosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

The diethyl 1-oxoindan-4-ylmethylphosphonate can be prepared in the following manner: a mixture of 0.5 g of 4-(bromomethyl)indan-1-one, 0.9 g of triethyl phosphate and 5 ml of xylene is heated at reflux for 5 hours. The reaction medium is concentrated in a rotary evaporator and then the residue is purified by chromatography on silica, eluting with an ethyl acetate-petroleum ether (85-15 by volume) mixture. 0.4 g of diethyl (2-bromo-1-oxoindan-4-yl)methylphosphonate is obtained in the form of a colourless oil [1H NMR spectrum in DMSO-d6, T=300K, δ in ppm (250 MHz): 1.20 (6H, t, J=6 Hz, 2 CH3), 2.70 (2H, m, CH2CO), 3.20 (2H, m, CH2), 3.38 (2H, d, J=22 Hz, PCH2), 4.00 (2H, q, J=6 Hz, OCH2), 7.45 (1H, t, J=7 Hz, arom. CH), 7.60 (2H, m, 2 arom. CH)].

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. concentrationThe reaction medium is concentrated in a rotary evaporator
  4. customthe residue is purified by chromatography on silica
  5. washeluting with an ethyl acetate-petroleum ether (85-15 by volume) mixture

Quellen und Nachweise

ORD-Eintrag
ord-8fe15a50bb974f7dbefa6a1c35ae26c0
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06100264

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