3-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-(2,2,2-trifluoro-ethoxy)-benzaldehyde → 1-ethyl-4,4,6-trimethyl-7-[2-(2,2,2-trifluoro-ethoxy)-5-vinyl-phenyl]-3,4-dihydro-1H-quinolin-2-one

HRID 1869555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869555
[CH2:1]([Li])CCC.[CH2:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH3:32])=[C:15]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=3[O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH:21]=O)[CH:16]=2)[C:11]([CH3:34])([CH3:33])[CH2:10][C:9]1=[O:35])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH3:32])=[C:15]([C:18]3[CH:19]=[C:20]([CH:21]=[CH2:1])[CH:23]=[CH:24][C:25]=3[O:26][CH2:27][C:28]([F:30])([F:31])[F:29])[CH:16]=2)[C:11]([CH3:34])([CH3:33])[CH2:10][C:9]1=[O:35])[CH3:7]

Komponenten

5

Edukt 2

HCID 579862973-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-(2,2,2-trifluoro-ethoxy)-benzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 579863101-ethyl-4,4,6-trimethyl-7-[2-(2,2,2-trifluoro-ethoxy)-5-vinyl-phenyl]-3,4-dihydro-1H-quinolin-2-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

In accordance with Scheme 16, to a suspension of methyltriphenylphosphonium bromide (3.27 mmol, 1.17 g) in 7.5 mL THF was added a solution of n-butyllithium in hexanes (1.6 M, 3.27 mmol, 2.04 mL) at −40° C. The reaction was warmed to −10° C. and stirred for 30 min. The reaction mixture was cooled to −60° C. and then Compound 1D (0.14 mmol, 0.06 g), in 7.5 mL THF, was added dropwise. The yellow suspension was allowed to stir at r.t. overnight and then quenched by adding 1 mL H2O. It was extracted with EtOAc and was washed with brine. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo. The yellow oil thus obtained was then purified by column chromatography (3.5:1 hexanes/EtOAc) to obtain 1-ethyl-4,4,6-trimethyl-7-[2-(2,2,2-trifluoro-ethoxy)-5-vinyl-phenyl]-3,4-dihydro-1H-quinolin-2-one as a colorless thick gum (0.61 g, 94% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to −60° C.
  2. stirringto stir at r.t. overnight
  3. customquenched
  4. additionby adding 1 mL H2O
  5. extractionIt was extracted with EtOAc
  6. washwas washed with brine
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent was removed in vacuo
  11. customThe yellow oil thus obtained
  12. customwas then purified by column chromatography (3.5:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6eb20adead9b41e1b9a3e4ec45244da3
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638533B2

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