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

HRID 36157

反応式

HRID 36157 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d0859d05e5c4869a8c8a58255ed0ec4
出典データセット
uspto-grants-1995_05
特許番号
US05412141

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