Ethyl Acetate → Ethyl 10-(3-iodophenoxy)-undecanoate

HRID 974762

反応式

HRID 974762 の反応式
Br[CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[I:17][C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[I:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 264833Ethyl 10-bromoundecanoate

生成物 1

HCID 15343343Ethyl 10-(3-iodophenoxy)-undecanoate収率 33.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
75 °C

実験手順

To a stirred solution of ethyl 10-bromoundecanoate (9.7 g, 33.0 mmol) in dry DMF (66 ml) was added 3-iodophenol (7.99 g, 36.3 mmol) and potassium carbonate (5.02 g, 37.6 mmol). The reaction was immersed in an oil bath which was warmed to 75° C. over 0.5 hr. After stirring for 14 hrs under an N2 atmosphere, the oil bath temperature was increased to 85° C. After stirring for an additional 4 hrs at 85° C., the reaction was allowed to cool, diluted with DMF (200 ml), filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up in ether (500 ml). The organic phase was washed with water (100 ml), 1M aqueous sodium hydroxide (100 ml), water (2×100 ml) and brine (100 ml), dried (Na2SO4), filtered and evaporated in vacuo to provide crude ethyl 10-(3-iodophenoxy)undecanoate which was contaminated with olefinic esters. Flash column chromatography (silica, 1-2%; EtOAc in hexanes) provide ethyl 10-(3-iodophenoxy)-undecanoate as a clear oil (4.75 g, 33.3%).

後処理

  1. customThe reaction was immersed in an oil bath
  2. temperaturethe oil bath temperature was increased to 85° C
  3. stirringAfter stirring for an additional 4 hrs at 85° C.
  4. temperatureto cool
  5. filtrationfiltered through a pad of celite
  6. customevaporated in vacuo
  7. washThe organic phase was washed with water (100 ml), 1M aqueous sodium hydroxide (100 ml), water (2×100 ml) and brine (100 ml)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto provide crude ethyl 10-(3-iodophenoxy)undecanoate which

出典と根拠

ORDレコード
ord-1acf029d0521479384144993a7ce67e1
出典データセット
uspto-grants-1997_03
特許番号
US05607660

関連ノート

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