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Imidazole → 3-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropionic acid ethyl ester

HRID 1847019
ノート
印刷プレビュー

反応式

HRID 1847019 の反応式
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([F:8])[CH2:6][OH:7])[CH3:2].N1C=CN=C1.[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([F:8])[CH2:6][O:7][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 13572114Ethyl 2-fluoro-3-hydroxypropanoateHCID 86585896Sodium bicarbonate water

生成物 1

HCID 867249473-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A crude product of 2-fluoro-3-hydroxypropionic acid ethyl ester (13.06 g) was dissolved in dichloromethane (300 ml). Imidazole (17.2 g, 252.57 mmol) and tert-butyldiphenylsilyl chloride (25 ml, 96.14 mmol) were added to the solution under cooling on ice, and the reaction solution was stirred for 18 hours while raising the reaction solution temperature to room temperature. Saturated sodium bicarbonate water was added to the reaction solution and the resultant was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 17.98 g (three steps, 57%) of the title compound in the form of a colorless clear oily product.

後処理

  1. temperatureunder cooling on ice
  2. extractionthe resultant was extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-a23be69496cf4a2096d9246d8dc98172
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952010B2

反応ノート

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