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

HRID 1492303

Reaktionsgleichung

Reaktionsgleichung von HRID 1492303
[H-].[Na+].[CH2:3]([C:5]1[NH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[C:13](=[O:15])[CH:14]=1)[CH3:4].[H][H].Br[CH2:19][C:20]1[CH:38]=[CH:37][C:23]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:22][CH:21]=1>CN(C=O)C.O>[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:19][C:20]2[CH:38]=[CH:37][C:23]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:22][CH:21]=2)[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[CH3:4]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 149504752-Ethyl-5,6,7,8-tetrahydroquinolin-4(1H)-oneHCID 18952399Ethyl 2-(4-bromomethylphenoxy)phenylacetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 18952389Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetateAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil; 63 mg) was added to a solution of compound D (254 mg) in DMF (5 ml). When evolution of hydrogen ceased, a solution of compound C (500 mg) in DMF (5 ml) was added and the solution was left to stand for 20 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2×25 ml). The combined extracts were washed with water (25 ml), followed by saturated sodium chloride solution (25 ml) and then dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), to give ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate (A) (265 mg), as an oil which solidified on standing, m.p. 89°-90° C. (after trituration with hexane); NMR: 1.1-1.35(2×t, 6H), 1.7-1.9(m, 4H), 2.6(t, 2H), 2.7(q, 2H), 2.85(t, 2H), 4.1-4.3(m, 2H), 5.0(s, 2H), 5.6(s, 1H), 6.5(s, 1H), 7.0(d, 2H), 7.25-7.5(m, 5H), 7.55-7.65(m, 2H).

Aufarbeitung

  1. waitthe solution was left
  2. extractionthe mixture was extracted with ethyl acetate (2×25 ml)
  3. washThe combined extracts were washed with water (25 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-411f1f1d6b3446cebf4f363d6c1ce3de
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05373015

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