Aluminium lithium hydride → 2-(4-Chlorophenyl)-2,2-difluoroethanol

HRID 54250ノート

反応式

HRID 54250 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:21])([F:20])[C:15](OCC)=[O:16])=[CH:10][CH:9]=1>C(OCC)C>[F:21][C:14]([F:20])([C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)[CH2:15][OH:16]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 21468011Ethyl 2-(4-Chlorophenyl)-2,2-difluoroacetate

生成物 1

HCID 232378442-(4-Chlorophenyl)-2,2-difluoroethanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
25 °C

実験手順

Lithium aluminum hydride, 2.4 grams (0.063 mole), is placed in a reaction vessel, and 200 mL of diethyl ether is added dropwise with stirring. To this is added dropwise a solution of 22.8 grams (0.097 mole) of ethyl 4-chlorophenyldifluoroacetate (prepared by methods taught by W. J. Middleton et al., J. Org. Chem., (1980), 45, 2883-2887) in 100 mL of diethyl ether, while maintaining the reaction mixture temperature at about 25° C. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 36 hours. The reaction is then quenched by the careful dropwise addition of an aqueous solution of 10% sodium hydroxide. The reaction mixture is slowly made acidic with aqueous 2N hydrochloric acid and then is diluted with 200 mL of water. The organic layer is separated, and the aqueous layer is washed with two 300 mL portions of diethyl ether. The organic layer and the diethyl ether washes are combined and washed with one 250 mL portion of an aqueous solution saturated with sodium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 2,2-difluoro-2-(4-chlorophenyl)ethanol.

後処理

  1. additionUpon completion of addition
  2. stirringthe reaction mixture is stirred at ambient temperature for about 36 hours
  3. customThe reaction is then quenched by the careful dropwise addition of an aqueous solution of 10% sodium hydroxide
  4. additionis diluted with 200 mL of water
  5. customThe organic layer is separated
  6. washthe aqueous layer is washed with two 300 mL portions of diethyl ether
  7. washwashed with one 250 mL portion of an aqueous solution saturated with sodium chloride
  8. dry with materialThe organic layer is dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated under reduced pressure

出典と根拠

ORDレコード
ord-70bad8e5400b4f1ea01fe9649e17ad86
出典データセット
uspto-grants-1997_04
特許番号
US05622954

反応ノート

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