Sodium Iodide → 2-(6-Iodohexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester

HRID 2210085Notes

Reaction equation

HRID 2210085 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]OS(C)(=O)=O)=[CH:10][CH:9]=[CH:8][C:7]=1[O:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].[I-:32].[Na+].C(#N)C>CCOCC>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[C:7]([O:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:8][CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][I:32]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 54145829HCID 54145829, compound

Product 1

HCID 152965542-(6-Iodohexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl esterYield 97.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10.81 g (ca. 23.37 mmol) of crude 2-(4-methoxy-4-oxobutoxy)-6-[6[(methylsulfonyl)oxy]hexyl]benzenepropanoic acid methyl ester (preceding example), 7.01 g (46.7 mmol) of anhydrous sodium iodide, and 44 mL of dry acetonitrile was stirred at room temperature for 17 hr and then refluxed for 3.5 hr. After being cooled, the mixture was diluted with 200 mL of ether and filtered with suction. The solids were washed thoroughly with ether. The filtrate and washes were combined and washed with 12% aqueous sodium bisulfite, and work-up was completed in the usual manner. There was obtained 11.14 g (97.3%) of 2-(6-iodohexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester as a yellow oil.

Workup

  1. temperaturerefluxed for 3.5 hr
  2. temperatureAfter being cooled
  3. filtrationfiltered with suction
  4. washThe solids were washed thoroughly with ether
  5. washwashed with 12% aqueous sodium bisulfite

Sources & evidence

ORD record
ord-0d63cdadd1d7456abe8705eb1c8ca18e
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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