Acetic Acid → [1-Cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester

HRID 252444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252444
[C:1]([CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])#[N:2].C([O-])(=O)C.[NH4+].C(O)(=O)C.[O:21]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[CH2:6]([O:5][P:4]([C:3]([C:1]#[N:2])=[CH:27][CH:24]1[CH2:25][CH2:26][O:21][CH2:22][CH2:23]1)(=[O:11])[O:8][CH2:9][CH3:10])[CH3:7]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 75676Diethyl (cyanomethyl)phosphonateHCID 517165Ammonium AcetateHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Produkt 1

HCID 72481733[1-Cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of diethyl cyanomethylphosphonate (50.0 g, 282 mmol), ammonium acetate (9.0 g, 117 mmol), acetic acid (9 ml) in toluene (200 mL), tetrahydropyran-4-carbaldehyde (32.2 g, 282 mmol) were added. The reaction mixture was stirred at room temperature for two hours and then heated at reflux for 1.5 hours. After cooling down, the reaction mixture was washed with saturated sodium bicarbonate solution three times, and brine one time and then dried over magnesium sulfate. The reaction mixture was filtered and concentrated to yield a residue. The residue was purified by Kugelrohr distillation to yield [1-cyano-2-(tetrahydropyran-4-yl)-vinyl]-phosphonic acid diethyl ester as a colorless oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter cooling down
  4. washthe reaction mixture was washed with saturated sodium bicarbonate solution three times, and brine one time
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe reaction mixture was filtered
  7. concentrationconcentrated
  8. customto yield a residue
  9. distillationThe residue was purified by Kugelrohr distillation

Quellen und Nachweise

ORD-Eintrag
ord-1ffbf3dc009849c181d4187c2cd13518
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868022B2

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