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Sodium Chloride → Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate

HRID 1492305
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Reaktionsgleichung

Reaktionsgleichung von HRID 1492305
Br[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1.[CH2:22]([C:24]1[N:33]=[C:32]([CH2:34][CH3:35])[CH:31]=[C:30]2[C:25]=1[CH2:26][CH2:27][C:28](=O)N2)C.CC(C)([O-:40])C.[K+].O1CCOCCOCCOCCOCCOCC1.[Cl-].[Na+]>O1CCCC1>[CH2:34]([C:32]1[CH:31]=[C:30]([O:40][CH2:2][C:3]2[CH:21]=[CH:20][C:6]([O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=2)[C:25]2[CH2:26][CH2:27][CH2:28][CH2:22][C:24]=2[N:33]=1)[CH3:35]
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Komponenten

7

Edukt 5

HCID 5234Sodium ChlorideHCID 2855718-Crown-6HCID 18952399Ethyl 2-(4-bromomethylphenoxy)phenylacetateHCID 200942545,7-diethyl-3,4-dihydro-1,6-naphthyridin-2(1H)-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 18952389
Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate
Ausbeute 18,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of compound C (2.34 g), 5,7-diethyl-1,2,3,4-tetrahydro-1,6-naphthyridin-2-one (1.02 g), potassium t-butoxide (0.57 g) and 1,4,7,10,13,16-hexaoxacyclooctadecane (132 mg) in dry tetrahydrofuran (50 ml) was heated under reflux for 36 hours. Saturated sodium chloride solution (100 ml) was added and the mixture was extracted with ether (2×100 ml). The combined extracts were dried (MgSO4) and concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (3:7 v/v), to give methyl 2-[4-((5,7-diethyl-2-oxo-1,2,3,4-tetrahydro-1,6-naphthyridin-1-yl)methyl)phenoxy]phenylacetate (A) (0.41 g) as an oil; NMR (d6 -DMSO): 1.05-1.25(2×t, 6H), 2.45-2.9(m, 8H), 3.6(s, 3H), 5.0(s, 2H), 5.95(s, 1H), 6.5-7.5(m, 10H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 36 hours
  3. extractionthe mixture was extracted with ether (2×100 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated by evaporation
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (3:7 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-3d1a8b0026aa4c1880f48e5a1a22025c
Quelldatensatz
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05373015

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