Sodium Iodide → 6-[6-(1-Methoxycarbonyl-ethyl)-naphthalen-2-yloxy]-hexanoic acid methyl ester

HRID 2169695Notes

Reaction equation

HRID 2169695 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH:7]=1)[CH3:5].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33]>CC(C)=O>[CH3:35][O:34][C:32](=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][O:16][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH:4]([C:3]([O:2][CH3:1])=[O:17])[CH3:5])[CH:7]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 5988972-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl esterHCID 4170292Methyl 6-Bromohexanoate

Product 1

HCID 592539896-[6-(1-Methoxycarbonyl-ethyl)-naphthalen-2-yloxy]-hexanoic acid methyl esterYield 55.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester 6 (150 g, 652 mmol), anhydrous K2CO3 (480 gr, 3.473 mol) and sodium iodide (22.5 grams, 150 mmol) in anhydrous acetone (2000 ml) was added methyl 6-bromohexanoate (216 g, 1.033 mol) and refluxed for 60 hours. Acetone was distilled off and water (1500 ml) was added. Crude 9 was extracted into ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 9 (130 g, 55.6%) as a light yellow syrup. The structure was confirmed with NMR.

Workup

  1. temperaturerefluxed for 60 hours
  2. distillationAcetone was distilled off
  3. additionwater (1500 ml) was added
  4. extractionCrude 9 was extracted into ethyl acetate
  5. dry with materialdried over Na2SO4
  6. distillationdistilled
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2c1090472eef4e90b9cbb0eaaeadd85c
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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