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

HRID 731013Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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)).

Workup

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

Sources & evidence

ORD record: ord-533ec3b654de4d8fa2a3daa7a17c3682
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582781B2

Reaction notes

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