Sodium hydride → (E)-3-[7-(1-phenylethoxy)-benzofuran-2-yl]-but-2-enoic acid-diethylamide

HRID 660420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660420
[H-].[Na+].[CH2:3]([N:5]([CH2:13][CH3:14])[C:6](=[O:12])[CH2:7]P(O)(O)=O)[CH3:4].[C:15]([C:18]1[O:22][C:21]2[C:23]([O:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])=[CH:24][CH:25]=[CH:26][C:20]=2[CH:19]=1)(=O)[CH3:16].[NH4+].[Cl-]>C1COCC1>[CH2:3]([N:5]([CH2:13][CH3:14])[C:6](=[O:12])/[CH:7]=[C:15](/[C:18]1[O:22][C:21]2[C:23]([O:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])=[CH:24][CH:25]=[CH:26][C:20]=2[CH:19]=1)\[CH3:16])[CH3:4]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 114032442-Acetyl-7-(1-phenylethoxy)benzo[b]furanHCID 18756985[(Diethylcarbamoyl)methyl]phosphonic acid

Produkt 1

HCID 11773324(E)-3-[7-(1-phenylethoxy)-benzofuran-2-yl]-but-2-enoic acid-diethylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

While replacing with nitrogen, NaH (0.13 g, 0.0054 mol) was suspended in absolute THF (20 mL), and N,N-diethylphosphonoacetamide (1.36 g, 0.0054 mol)/absolute THF (10 mL) was added dropwise at 0° C. Then, 2-acetyl-7-(1-phenylethoxy)benzo[b]furan (1.0 g, 0.0036 mol)/absolute THF (20 mL) was added dropwise. After stirring for 6 h while allowing to warm to room temperature, the disappearance of the starting materials was confirmed by TLC. The reaction mixture was poured into saturated aqueous NH4Cl solution, mixed and THF was evaporated under reduced pressure. The residue was extracted with ethyl acetate, washed with brine, dried over absolute magnesium sulfate, and evaporated under reduced pressure to give a pale-yellow oil. The obtained oil was purified by column chromatography to give the title compound as a pale-yellow oil. (0.75 g, 55.6%)

Aufarbeitung

  1. additionmixed
  2. customTHF was evaporated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over absolute magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give a pale-yellow oil
  8. customThe obtained oil was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6a1d8ea801224706b1af478186b712b0
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084492B2

Notizen zur Reaktion

Wird geladen…