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Chlorotrimethylsilane → Diethyl [2-(2-Fluorophenyl)-2-oxoethyl]phosphonate

HRID 48320
ノート
印刷プレビュー

反応式

HRID 48320 の反応式
[CH2:1]([O:3][P:4]([CH2:9][C:10]([OH:12])=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(N(CC)CC)C.Cl[Si](C)(C)C.[Cl-].[Mg+2].[Cl-].[F:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1C(Cl)=O>C1(C)C=CC=CC=1>[CH2:7]([O:6][P:4]([CH2:9][C:10]([C:30]1[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=1[F:28])=[O:12])(=[O:5])[O:3][CH2:1][CH3:2])[CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 36704(Diethoxyphosphinyl)acetic acidHCID 5360315Magnesium Chloride

生成物 1

HCID 86585808Diethyl [2-(2-Fluorophenyl)-2-oxoethyl]phosphonate収率 64.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 2.34 g (11.9 mmol) of diethylphosphonoacetic acid in toluene at 0° C. was added 4.82 g (47.7 mmol) of triethylamine followed by 1.94 g (17.9 mmol) of chlorotrimethylsilane. The mixture was stirred at ambient temperature for 1 hour, then 1.13 g (11.9 mmol) of magnesium chloride was added and the mixture was stirred for a further 1 hour. To the mixture was added 2.0 g (14.3 mmol) of 2-fluorobenzoyl chloride and the mixture was stirred for 72 hours. The mixture was partitioned between 200 ml of water and 250 ml, 100 ml of dichloromethane. The combined organic portions were dried (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography eluting with 3-5% methanol/dichloromethane to give 2.1 g (64%) of [2-(2-fluorophenyl)-2-oxoethyl]phosphonic acid diethyl ester as a colorless oil; MS: m/e 274.9 [M+H]+.

後処理

  1. stirringthe mixture was stirred for a further 1 hour
  2. stirringthe mixture was stirred for 72 hours
  3. customThe mixture was partitioned between 200 ml of water and 250 ml, 100 ml of dichloromethane
  4. dry with materialThe combined organic portions were dried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with 3-5% methanol/dichloromethane

出典と根拠

ORDレコード
ord-b0e8ef5bf537437c815fb0e222c755ee
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06703387B2

反応ノート

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