Water → Di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentanedioate

HRID 989625

Reaktionsgleichung

Reaktionsgleichung von HRID 989625
[C:1]([O:5][PH:6]([CH2:8][CH:9]([CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:30])[C:27]([CH3:29])=[CH2:28].[H-].[Na+].O>C1COCC1.CCOCC>[CH2:32]([O:31][C:26]([CH:27]([CH3:29])[CH2:28][P:6]([CH2:8][CH:9]([CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 17236Benzyl methacrylateHCID 24758Sodium hydrideHCID 178451016HCID 178451016, Verbindung

Produkt 1

HCID 18418074Di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentanedioateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of di-tert-butyl 2-[(tert-butoxy-phosphinyl)methyl]pentane-l,5-dioate (13.62 g, 36.0 mmol) and benzyl methacrylate (6.35 g, 36.0 mmol) in THF (100 ml) under nitrogen was added sodium hydride (0.14 g, 60% dispersion in oil, 3.60 mmol). After three hours, the reaction mixture was poured into water (300 ml) and ether (100 ml) was added. The organic layer was separated and retained, and the aqueous layer was washed again with ether (100 ml). The combined organic extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography and the product was eluted with 2:3 EtOAc/Hexane. The solvent was removed under reduced pressure leaving a clear oil (10.5 g, 53%). 1H NMR (CDCl3) : δ 1.3 (m, 3H), 1.5 (m, 27H), 1.7 (m, 2H), 1.9 (m, 2H), 2.2 (m, 4H), 2.6 (m, 1H), 2.9 (m, 1H), 5.1 (m, 2H), 7.3 (m, 5H).

Aufarbeitung

  1. additionwas added
  2. customThe organic layer was separated
  3. washthe aqueous layer was washed again with ether (100 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by column chromatography
  7. washthe product was eluted with 2:3 EtOAc/Hexane
  8. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35c7d8c9469744a18055546c3631a8ae
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458775B1

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