[1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester → HCID 68738694, Verbindung

HRID 658068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658068
C(OP([CH:9]([C:17]#[N:18])[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)(=O)OCC)C.[O:19]1[CH2:24][CH2:23][CH2:22][O:21][CH:20]1[C:25]1[CH:26]=[C:27]([S:31][C:32]2[C:33]([F:43])=[CH:34][C:35]([N+:40]([O-:42])=[O:41])=[C:36]([CH:39]=2)[CH:37]=O)[CH:28]=[CH:29][CH:30]=1>C1COCC1.C(OCC)(=O)C>[O:19]1[CH2:24][CH2:23][CH2:22][O:21][CH:20]1[C:25]1[CH:26]=[C:27]([S:31][C:32]2[C:33]([F:43])=[CH:34][C:35]([N+:40]([O-:42])=[O:41])=[C:36]([CH:37]=[C:9]([CH2:10][CH:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[C:17]#[N:18])[CH:39]=2)[CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 2

HCID 86634265[1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl esterHCID 86634267HCID 86634267, Verbindung

Produkt 1

HCID 68738694HCID 68738694, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

[1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester (0.614 g, 2.23 mmol), prepared as described in Example 1, Steps A and B, was dissolved in THF (75 mL) and the resulting mixture cooled to 0° C. Lithium (bistrimethylsilyl)amide (2.2 mL, 2.2 mmol, [1M]) was then added dropwise. The resulting mixture was stirred 15 min, and then 5-(3-[1,3]dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-benzaldehyde (0.6 g, 1.65 mmol) was added. Stirring was continued at room temperature overnight. The resulting mixture was then diluted with ethyl acetate and washed with saturated aqueous NaHCO3. The organic phase was separated and dried with MgSO4, and filtered. The solvent was removed to yield an oil, which was used in the next step without further purification.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued at room temperature overnight
  3. washwashed with saturated aqueous NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customto yield an oil, which
  9. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8274c3c6beed4d718d3e7d46512f289f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076358B2

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