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

HRID 36157

Reaction equation

HRID 36157 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1d0859d05e5c4869a8c8a58255ed0ec4
Source dataset
uspto-grants-1995_05
Patent number
US05412141

Linked notes

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