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

HRID 731013노트

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HRID 731013 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86606435HCID 86606435, 화합물HCID 178505836HCID 178505836, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
0 °C

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-533ec3b654de4d8fa2a3daa7a17c3682
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582781B2

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