Ethyl Acetate → 1-(3-Iodophenoxy)-3,6,9-trioxadecane
Reaction equation
CS([CH:5]([OH:15])[CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])(=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:15][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14]Participants
Conditions
- Temperature
- 68 °C
Procedure
To a solution of 1-[(methanesulfonyl)-oxyl-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), 1 N 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
- customThe reaction was immersed in an oil bath
- waitat 82° C. for an additional 2 hrs
- temperatureAt the end of this period, the reaction was cooled
- filtrationfiltered through a pad of celite
- customevaporated in vacuo
- washwashed with water (200 ml), 1 N aqueous sodium hydroxide (200 ml) and brine (200 ml)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated in vacuo
- customto provide a light brown oil
Sources & evidence
- ORD record
- ord-fa7feb9a31d147e0a598dc652d9cfc17
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05310538
Reaction notes
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