Iodine → [1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

HRID 502862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502862
II.Br[CH2:4][CH2:5][CH:6]=[CH2:7].[CH2:8]([O:10][P:11]([C:16]([C:24]#[N:25])=[CH:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9].[NH4+].[Cl-]>C1COCC1.[Cu]I.C(OCC)(=O)C>[CH2:8]([O:10][P:11]([CH:16]([C:24]#[N:25])[CH:17]([CH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[CH2:7][CH2:6][CH:5]=[CH2:4])(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9]

Komponenten

8

Edukt 4

HCID 807IodineHCID 21241Homoallyl bromideHCID 25517Ammonium ChlorideHCID 72481733[1-Cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester

Produkt 1

HCID 59428163[1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a reaction flask, Mg (5.7 g) was placed in THF (50 mL) with an iodine chip. The reaction mixture was stirred vigorously, as 4-bromobutene (25 mL) was added. The reaction mixture was then heated slightly. After consumption of the Mg metal, the reaction mixture was cannulated into a flask containing a mixture of [1-cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester (21.78 g, 79.7 mmol) and CuI (0.3 g) in THF (30 mL). The reaction mixture was stirred for three hours and then worked up with saturated aqueous NH4Cl and ethyl acetate. The layers were separated, and the organic layer was dried with MgSO4, filtered, and evaporated in vacuo to yield the title compound as an oil.

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was then heated slightly
  3. customAfter consumption of the Mg metal
  4. customthe reaction mixture was cannulated into a flask
  5. additioncontaining
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried with MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0b3867c3ae8450c8aadb6b8f21760bd
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776882B2

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