5-Fluoro-2-nitrobenzaldehyde → HCID 68978639, Verbindung

HRID 658061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658061
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.[F:19][C:20]1[CH:21]=[CH:22][C:23]([N+:28]([O-:30])=[O:29])=[C:24]([CH:27]=1)[CH:25]=O>C1COCC1.C(OCC)(=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([N+:28]([O-:30])=[O:29])=[C:24]([CH:25]=[C:9]([CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:17]#[N:18])[CH:27]=1

Komponenten

5

Edukt 2

HCID 5870905-Fluoro-2-nitrobenzaldehydeHCID 86634265[1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester

Produkt 1

HCID 68978639HCID 68978639, 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 (5.4 g, 19.6 mmol) was dissolved in THF (100 mL) and cooled to 0° C. Lithium (bistrimethylsilyl)amide (20 mL, 20 mmol, [1M]) was the added dropwise. The resulting mixture was stirred 20 min, and then 5-fluoro-2-nitro-benzaldehyde (3.31 g, 19.6 mmol) was added. The resulting mixture was stirred at room temperature overnight, then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 solution. The organic phase was separated and dried with MgSO4 and filtered. The solvent was removed to yield an oil which was purified by silica column chromatography (120 g column, 20% EtOAc/heptane) to yield a solid.

Aufarbeitung

  1. additionadded dropwise
  2. stirringThe resulting mixture was stirred at room temperature overnight
  3. washwashed with saturated aqueous NaHCO3 solution
  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 purified by silica column chromatography (120 g column, 20% EtOAc/heptane)
  10. customto yield a solid

Quellen und Nachweise

ORD-Eintrag
ord-3502708835bf46edbbd2460ba8ddbfbb
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076358B2

Notizen zur Reaktion

Wird geladen…