Sodium Hydroxide → Ethyl hydrogen (E)-2-{4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate

HRID 2100072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100072
[C:1]1(=[C:8]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[P:17](=[O:24])([O:21]CC)[O:18][CH2:19][CH3:20])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[C:1]1(=[C:8]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[P:17](=[O:21])([OH:24])[O:18][CH2:19][CH3:20])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86613508Diethyl(E)-2-{-4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate

Produkt 1

HCID 11189110Ethyl hydrogen (E)-2-{4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonateAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of diethyl(E)-2-{-4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate (63) (0.051 g, 0.115 mmol) in EtOH (4 mL) was added aqueous NaOH (1 mL of a 5M solution, 5 mmol). The solution was heated to reflux for 4 h, then cooled to RT and concentrated. The residue was dissolved in water (1 mL) and the pH adjusted to ˜2 with 1 N aqueous HCl. The mixture was extracted with EtOAc (2×10 mL). The organics were dried (Na2SO4) and concentrated to provide compound 64 (0.041 g, 86%) as a waxy yellow solid. 1H NMR (DMSO-d6): δ 9.28 (s, 1H), 7.53 (d, J=8.1 Hz, 2H), 7.20 (dd, J=22.0 Hz, 17.6 Hz, 1H), 7.10 (d, J=8.1 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 6.65 (d, J=8.4 Hz, 2H), 6.41 (t, J=17.6 Hz, 1H), 3.90-3.84 (m, 2H), 2.20 (m, 4H), 1.50 (m, 8H), 1.18 (t, J=6.9 Hz, 3H). LRMS (ESI): m/z 411 (M−H)−.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in water (1 mL)
  5. extractionThe mixture was extracted with EtOAc (2×10 mL)
  6. dry with materialThe organics were dried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b977ae4e577346ee9e2334dcd85e9822
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569601B2

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