Imidazole → 1,1,1-Trifluoro-2-chloro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane

HRID 483725ノート

反応式

HRID 483725 の反応式
[F:1][C:2]([F:31])([F:30])[C:3]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=1)(O)[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1.N1C=CN=C1.S(Cl)([Cl:39])=O>C(#N)C>[F:1][C:2]([F:31])([F:30])[C:3]([Cl:39])([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=1)[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 145169431,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propan-2-ol

生成物 1

HCID 145169861,1,1-Trifluoro-2-chloro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane収率 70.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

A solution of 1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propan-2-ol (0.65 g) and imidazole (0.612 g) were dissolved in dry acetonitrile 30 cm3), and the solution cooled to ca. 0° C. Thionyl chloride (1.21 g) was added dropwise, with stirring. The reaction mixture was allowed to warm to the ambient temperature (ca. 22° C.) and was stirred for a further three hours. Analysis of the reaction mixture by thin layer chromatography and gas liquid chromatography at that time showed no starting tertiary alcohol to be present. The reaction mixture was quenched with water, and a small volume of saturated sodium chloride solution was added. The aqueous mixture was extracted four times with diethyl ether and, finally, once with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate and concentrated by evaporation of the solvent under reduced pressure to give an oil. The product was purified by column chromatography on a silica gel support, using n-hexane containing 6% by volume ethyl acetate as eluent, to give 1,1,1-trifluoro-2-chloro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane (0.48 g) as a colourless oil.

後処理

  1. temperatureto warm to the ambient temperature (ca. 22° C.)
  2. stirringwas stirred for a further three hours
  3. customThe reaction mixture was quenched with water
  4. additiona small volume of saturated sodium chloride solution was added
  5. extractionThe aqueous mixture was extracted four times with diethyl ether
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  7. concentrationconcentrated by evaporation of the solvent under reduced pressure
  8. customto give an oil
  9. customThe product was purified by column chromatography on a silica gel support

出典と根拠

ORDレコード
ord-90f2749ceb574525bc1db5463364a4f0
出典データセット
uspto-grants-1993_07
特許番号
US05225607

反応ノート

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