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

HRID 1492305Notes

Reaction equation

HRID 1492305 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 18952389Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetateYield 18.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-3d1a8b0026aa4c1880f48e5a1a22025c
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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