HCID 10358783, Verbindung → diethyl (Z)-4-hydroxybut-1-enylphosphonate

HRID 1708084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708084
[Si]([O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])(C(C)(C)C)(C)C>C(O)(=O)C.O>[OH:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19]

Komponenten

3

Edukt 1

HCID 10358783HCID 10358783, Verbindung

Produkt 1

HCID 10081772diethyl (Z)-4-hydroxybut-1-enylphosphonateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of diethyl (Z)-4-(t-butyldimethylsilyloxy)but-1-enylphosphonate (1.32 g, 4.09 mmol) in acetic acid-water (2:1) (35 ml) was stirred at room temperature for 2 hr. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1) to give diethyl (Z)-4-hydroxybut-1-enylphosphonate as a colourless liquid (0.5 g, 59%); νmax (film) 3380, 2980, 1720, 1620, 1390, 1230 and 1020 cm-1 ; δH (CDCl3) 1.33 (6H, t, J 7 Hz, CH3), 2.70 (2H, m, CH2), 3.15 (1H, s, OH), 3.73 (2H, t, J 7 Hz, CH2O ), 4.00 (4H, qu, J 7 Hz, CH3CH2), 5.70 (1H, dd, J 14 Hz and 20 Hz, PCH=CH), 6.60 (1H, ddt, J 7 Hz, 14 Hz and 54 Hz, PCH=CH) (Found: MH+ 209.0942. C8H17O4P requires MH+ 209.0943).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1)

Quellen und Nachweise

ORD-Eintrag
ord-888acce06a4045d1b3c23cd9c982e1f9
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05356886

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