Sodium Iodide → HCID 15086674, compound

HRID 2108270Notes

Reaction equation

HRID 2108270 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:9]=1.[CH2:30]([O:32][C:33](=[O:47])[C@@H:34]([CH3:46])[C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([OH:45])[CH:41]=2)[CH:36]=1)[CH3:31].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH2:30]([O:32][C:33](=[O:47])[C@@H:34]([CH3:46])[C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([O:45][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:10]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:9]=3)[CH:41]=2)[CH:36]=1)[CH3:31]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15086653HCID 15086653, compoundHCID 15086656HCID 15086656, compound

Product 1

HCID 15086674HCID 15086674, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.2 g (4.86 mmol) of 1-(6-bromohexyl)-3,4-bis(phenylmethoxy)benzene, 1.0 g (4.1 mmol) of (S)-alpha-methyl-6-hydroxy-2-naphthaleneacetic acid ethyl ester, 0.68 g (4.5 mmol) sodium iodide and 2.4 g (17.4 mmol) of potassium carbonate in 50 mL of acetone-50 mL of dimethylformamide was stirred at reflux for 23 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was purified by HPLC using 10% ethyl acetate-hexane to give 2.2 g (87% yield) of (S)-alpha-methyl-6-[6-[3,4-bis(phenylmethoxy)-phenyl]hexyloxy]-2-naphthaleneacetic acid ethyl ester as an oil. The nmr was consistent with the structure.

Workup

  1. temperatureat reflux for 23 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-1b8c100183954a4fa97eca349cb1df4f
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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