Water → 1-Chloro-2-(2,4-difluorophenyl)-3-pivaloyloxybutan-2-ol

HRID 731013ノート

反応式

HRID 731013 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[Mg]Br.[Cl:11][CH2:12][C:13](=[O:23])[C@H:14]([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:15].[Cl-].[NH4+].O>C1(C)C=CC=CC=1>[Cl:11][CH2:12][C:13]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([OH:23])[CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:20])([CH3:19])[CH3:21])[CH3:15]

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86606435HCID 86606435、化合物HCID 178505836HCID 178505836、化合物

生成物 1

HCID 231170411-Chloro-2-(2,4-difluorophenyl)-3-pivaloyloxybutan-2-ol収率 94%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

First, 8.9 mL (8.0 mmol) of a 0.9 M solution of 2,4-difluorophenylmagnesium bromide prepared by the same method as that in Example 3 was cooled to 0° C., and a solution of 0.83 g (4.0 mmol) of (R)-1-chloro-3-pivaloyloxybutan-2-one in 10 mL of toluene was added dropwise thereto over a period of 5 minutes. After the completion of the dropwise addition, stirring was continued for another 1 hour, and 20 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 (30 mL×2). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain 1.57 g of a crude product. A quantitative analysis was performed by HPLC. Thereby, the title compound was obtained in a yield of 94% ((2S,3R)/(2R,3R)=93/7 (the diastereomeric ratio was measured by HPLC under the same HPLC measurement conditions as those in Example 19)).

後処理

  1. additionAfter the completion of the dropwise addition
  2. waitwas continued for another 1 hour
  3. customthe reaction
  4. extractionextraction
  5. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  6. customto obtain 1.57 g of a crude product

出典と根拠

ORDレコード
ord-533ec3b654de4d8fa2a3daa7a17c3682
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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