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

HRID 1492303Notes

Reaction equation

HRID 1492303 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 18952389Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetateYield 41.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-411f1f1d6b3446cebf4f363d6c1ce3de
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

Loading…