Sodium hydride → Ethyl 4-[3-(4-{[benzyl(2-methyl-3-nitrophenyl)amino]methyl}phenoxy)phenoxy]butanoate

HRID 1370901Notes

Reaction equation

HRID 1370901 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:33]=[CH:32][C:23]([O:24][C:25]2[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=2)=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>CN(C=O)C.C(OCC)C>[CH2:1]([N:8]([CH2:19][C:20]1[CH:33]=[CH:32][C:23]([O:24][C:25]2[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=2)[O:31][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 185122603-(4-{[Benzyl(2-methyl-3-nitrophenyl)amino]methyl}phenoxy)phenol

Product 1

HCID 18512262Ethyl 4-[3-(4-{[benzyl(2-methyl-3-nitrophenyl)amino]methyl}phenoxy)phenoxy]butanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Example 61F (0.1000 g, 0.227 mmoles) in DMF (0.57 mL) was treated with NaH (0.0109 g, 0.27 mmoles, 60% dispersion). After 15 min, ethyl 4-bromobutyrate (0.039 mL, 0.27 mmoles) was added and the reaction was stirred overnight. The crude products were diluted with diethyl ether, washed with sat. NH4Cl, extracted with H2O (2×), washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (hexane to 7:1 hexane:ethyl acetate) to provide the title compound as a yellow oil.

Workup

  1. washwashed with sat. NH4Cl
  2. extractionextracted with H2O (2×)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (hexane to 7:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-056d418032db48fd85a6267786dfbb8a
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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