Water → 1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

HRID 731008ノート

反応式

HRID 731008 の反応式
[Cl:1][CH2:2][C:3](=[O:11])[C@H:4]([O:6][Si](C)(C)C)[CH3:5].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[Mg]Br.[Cl-].[NH4+].O>C1COCC1>[Cl:1][CH2:2][C:3]([C:16]1[CH:15]=[CH:14][C:13]([F:12])=[CH:18][C:17]=1[F:19])([OH:11])[CH:4]([OH:6])[CH3:5]

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 71415957(3R)-1-Chloro-3-[(trimethylsilyl)oxy]butan-2-oneHCID 178505836HCID 178505836、化合物

生成物 1

HCID 231170401-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 0.7 g (3.6 mmol) of (R)-1-chloro-3-(trimethylsilyloxy)butan-2-one in 5 mL of THF was cooled to 0° C., 5.4 mL (3.8 mmol) of a 0.7 M solution of 2,4-difluorophenylmagnesium bromide prepared by the same method as that in Example 3 was added dropwise thereto over a period of 10 minutes. After the completion of the dropwise addition, stirring was continued for another 5 hours, and 10 mL of a saturated aqueous solution of ammonium chloride was added to stop the reaction. Furthermore, 10 mL of water was added, and extraction was performed with ethyl acetate (20 mL×2). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain 1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol. A quantitative analysis was performed by HPLC (under the same HPLC measurement conditions as those in Example 6). As a result, the yield was determined to be 87% ((2S,3R)/(2R,3R)=41/59).

後処理

  1. additionwas added dropwise
  2. additionAfter the completion of the dropwise addition
  3. waitwas continued for another 5 hours
  4. customthe reaction
  5. extractionextraction
  6. dry with materialAfter drying over anhydrous sodium sulfate, concentration

出典と根拠

ORDレコード
ord-a60c73777d054bffbe5b7debb14e95ad
出典データセット
uspto-grants-2009_09
特許番号
US07582781B2

反応ノート

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