Ethyl bromoacetate → Ethyl [(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]acetate

HRID 1992981Notes

Reaction equation

HRID 1992981 reaction equation
[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.C([O-])([O-])=O.[K+].[K+].[CH2:34]([O:36][C:37](=[O:40])[CH2:38]Br)[CH3:35]>CC(C)=O>[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:38][C:37]([O:36][CH2:34][CH3:35])=[O:40])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 685394164-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol

Product 1

HCID 86616670Ethyl [(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]acetateYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A round-bottomed flask was charged with 4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol (233) (0.150 g, 0.421 mmol), K2CO3 (0.116 g, 0.842 mol), acetone, and ethylbromoacetate (0.105 g, 0.632 mmol) under N2. The reaction mixture was refluxed for 5 h and cooled at room temperature. Reaction mixture was filtered and concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using hexanes:EtOAc (19:1 to 9:1) as an eluent to give 0.177 g (95%) of the title compound (234) as a white foam. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=9.2 Hz, 1H), 7.54 (s, 1H), 7.29-7.22 (m, 3H), 7.13-7.11 (m, 3H), 7.05 and 7.03 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.63 (d, J1=9.2 Hz, 2H), 6.50 (d, J1=9.2 m, 2H), 4.48 (s, 2H), 4.24 (q, J=3.8 Hz, 2H), 3.93 (s, 3H), 2.23 (s, 3H), 1.27 (t, J=3.00 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customReaction mixture
  3. filtrationwas filtered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customThe product was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-31eff791c8c6423a8e2212fbf3cf297d
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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