Ethyl Acetate → 1-(3-Iodophenoxy)-3,6,9-trioxadecane

HRID 2396410Notes

Reaction equation

HRID 2396410 reaction equation
CS([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])(=O)=O.[I:16][C:17]1[CH:18]=[C:19](O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.CCCCCC>[I:16][C:17]1[CH:22]=[C:21]([CH:20]=[CH:19][CH:18]=1)[O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 126212722-(2-(2-Methoxyethoxy)ethoxy)ethyl methanesulfonate

Product 1

HCID 189870031-(3-Iodophenoxy)-3,6,9-trioxadecaneYield 61.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
68 °C

Procedure

To a solution of 1-[(methanesulfonyl)-oxy]-3,6,9-trioxadecane (11.6 g, 47.9 mmol) in dry DMF (145 ml) was added 3-iodophenol (10.6 g, 48.2 mmol) and potassium carbonate (6.6 g, 47.8 mmol). The reaction was immersed in an oil bath which was warmed to 68° C. over a period of 0.5 hr. The reaction was stirred at this temperature under an N2 atmosphere for 16 hrs and then at 82° C. for an additional 2 hrs. At the end of this period, the reaction was cooled, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into ethyl acetate (500 ml), washed with water (200 ml), 1N aqueous sodium hydroxide (200 ml) and brine (200 ml), dried (Na2SO4), filtered and evaporated in vacuo to provide a light brown oil. Flash column chromatography (silica, 1:3 to 1:2; EtOAc:hexane) provided 1 -(3-iodophenoxy)-3,6,9-trioxadecane as a light yellow oil (10.8 g, 37.1%).

Workup

  1. customThe reaction was immersed in an oil bath
  2. waitat 82° C. for an additional 2 hrs
  3. temperatureAt the end of this period, the reaction was cooled
  4. filtrationfiltered through a pad of celite
  5. customevaporated in vacuo
  6. washwashed with water (200 ml), 1N aqueous sodium hydroxide (200 ml) and brine (200 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto provide a light brown oil

Sources & evidence

ORD record
ord-768ad146edfe4a3d80b37eefadb6d2a1
Source dataset
uspto-grants-1996_02
Patent number
US05492687

Reaction notes

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