Dibenzoylmethane → (3,3-Dibenzoylpropylidene)bisphosphonic acid tetraethyl ester

HRID 36157

Reaktionsgleichung

Reaktionsgleichung von HRID 36157
[CH2:1]([O:3][P:4]([C:9]([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=[CH2:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:19]([CH2:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1CCN2C(=NCCC2)CC1>C1COCC1.C(OCC)(=O)C>[CH2:16]([O:15][P:11]([CH:9]([P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])[CH2:10][CH:27]([C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:18])[O:12][CH2:13][CH3:14])[CH3:17]

Komponenten

6

Edukt 3

HCID 8433DibenzoylmethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11022954Tetraethyl vinylidene phosphonate

Produkt 1

HCID 15229422(3,3-Dibenzoylpropylidene)bisphosphonic acid tetraethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethenylidenebisphosphonic acid tetraethyl ester (I, 3.00 g), dibenzoyl methane (II, 2.30 g), and DBU (0.25 ml) are heated to 50° in THF (20 ml) for 15 min. The reaction mixture is cooled, diluted with ethyl acetate, filtered through magnesium sulfate and concentrated under reduced pressure. The concentrate is chromatographed eluting with ethyl acetate, ethyl acetate/acetone (1/1). The appropriate fractions are pooled and concentrated to give the title compound, MS (m/e) 524 (M+), 419, 387, 373, 268 and 224; IR (neat) 2982, 1736, 1696, 1674, 1594, 1580, 1448, 1392 and 1253 cm-1 ; NMR (CDCl3) 8.07, 7.58, 7.46, 6.18, 4.17, 2.65 and 1.29 δ.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered through magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate is chromatographed
  5. washeluting with ethyl acetate, ethyl acetate/acetone (1/1)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1d0859d05e5c4869a8c8a58255ed0ec4
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412141

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