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

HRID 128891

反応式

HRID 128891 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
68 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7e492b043bfe4ec695a995ef1030b663
出典データセット
uspto-grants-1995_11
特許番号
US05466435

関連ノート

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