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

HRID 36157

반응식

HRID 36157 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d0859d05e5c4869a8c8a58255ed0ec4
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412141

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