Ethyl Acetate → [1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester

HRID 658060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658060
[CH2:1]([O:3][P:4]([C:9]([C:17]#[N:18])=[CH:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[BH4-].[Na+].[OH-].[Na+].C(OCC)(=O)C>CO>[CH2:1]([O:3][P:4]([CH:9]([C:17]#[N:18])[CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 72481733[1-Cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester

Produkt 1

HCID 86634265[1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of [1-cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester (7.45 g, 27.1 mmol) in methanol (200 mL) was added sodium borohydride (5 g, 135 mmol, 5 pellets), portion wise over 1.5 hours. The resulting mixture was stirred an additional 2 hours. The solvent was evaporated in vacuo to yield an oil, to which was added 0.1N NaOH and ethyl acetate. The layers were separated, and the organic layer was dried with MgSO4 and filtered. The solvent was removed to yield an oil which was purified via silica column chromatography (50% EtOAc/heptane) to yield an oil.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customto yield an oil
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customto yield an oil which
  8. customwas purified via silica column chromatography (50% EtOAc/heptane)
  9. customto yield an oil

Quellen und Nachweise

ORD-Eintrag
ord-4b6db4dfbb044098bc14da3628564532
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076358B2

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