Sodium Iodide → HCID 15086658, compound

HRID 2108265Notes

Reaction equation

HRID 2108265 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH3:30][O:31][C:32](=[O:46])[C@@H:33]([CH3:45])[C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[C:39]([OH:44])[CH:40]=2)[CH:35]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:30][O:31][C:32](=[O:46])[C@@H:33]([CH3:45])[C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:9]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:40]=2)[CH:35]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 15086654HCID 15086654, compound

Product 1

HCID 15086658HCID 15086658, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.25 g (7.17 mmol) of 1-(6-bromohexyl)-2,3-bis-(phenylmethoxy)benzene, 1.50 g (6.5 mmol) of (S)-alpha-methyl-6-hydroxy-2-naphthaleneacetic acid methyl ester, 1.08 g (7.17 mmol) of sodium iodide and 2.70 g (19.6 mmol) of potassium carbonate in 60 mL of acetone - 6 mL of dimethylformamide was stirred at reflux for 48 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was purified by HPLC using 20% ethyl acetate-hexane to give 3.24 g (75% yield) of (S)-alpha-methyl-6-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]-2-naphthaleneacetic acid methyl ester as an oil. The nmr and mass spectra were consistent with the structure.

Workup

  1. temperatureat reflux for 48 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-008846c8861f49c6bc389cf765bd67f0
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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