Lithium diisopropylamide → N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamide

HRID 1871531

Reaktionsgleichung

Reaktionsgleichung von HRID 1871531
C(OP([CH2:9][C:10](=[O:15])[N:11]([O:13][CH3:14])[CH3:12])(=O)OCC)C.C([N-]C(C)C)(C)C.[Li+].[CH:24]1([O:29][C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=2[O:38][CH3:39])[CH:33]=O)[CH2:28][CH2:27][CH2:26][CH2:25]1>O1CCCC1.O>[CH3:14][O:13][N:11]([CH3:12])[C:10](=[O:15])[CH:9]=[CH:33][C:32]1[CH:35]=[CH:36][C:37]([O:38][CH3:39])=[C:30]([O:29][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:31]=1

Komponenten

6

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 2773719Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

Produkt 1

HCID 54075299N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamideAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of diethyl(N-methoxy-N-methyl-carbamoylmethyl)phosphonate (2.60 g, 10.90 mmol) in dry tetrahydrofuran (50 ml) at -78° C. was added lithium diisopropylamide (1.5M solution in cyclohexane, 7.33 ml, 11 mmol) dropwise over 3 minutes. The resulting solution was stirred at -78° C. for 30 minutes, after which time 3-cyclopentyloxy-4-methoxybenzaldehyde (1.5 g, 6.81 mmol) in dry tetrahydrofuran (5 ml) was added in one portion. The reaction was allowed to warm to room temperature and stirring continued overnight. After which time the reaction mixture was diluted with water (25 ml) and the tetrahydrofuran removed in vacuo. The aqueous residue was diluted with brine (25 ml) and extracted with methylene chloride (3×60 ml). The organic extracts were dried (Na2SO4) and evaporated in vacuo to give a yellow liquid. The liquid was purified by flash chromatography (SiO2 ; hexane/ethyl acetate (65:35)) to afford the title compound as a pale yellow liquid (1.986 g).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirring continued overnight
  3. customthe tetrahydrofuran removed in vacuo
  4. additionThe aqueous residue was diluted with brine (25 ml)
  5. extractionextracted with methylene chloride (3×60 ml)
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a yellow liquid
  9. customThe liquid was purified by flash chromatography (SiO2 ; hexane/ethyl acetate (65:35))

Quellen und Nachweise

ORD-Eintrag
ord-0153198dec1941f3aecec2bd4eb60fa3
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103749

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