Hydrochloric Acid → Ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate

HRID 860412

反応式

HRID 860412 の反応式
[Cl-].[Mg+2].[Cl-].[O:4]=[C:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.Cl>O1CCCC1.C(OCC)(=O)C.N1C=CC=CC=1>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([CH:6]([C:5](=[O:4])[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:25])=[CH:22][CH:21]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 678794-Fluorobenzoyl chlorideHCID 225855Ethyl 3-oxo-4-phenylbutanoateHCID 5360315Magnesium Chloride

生成物 1

HCID 57444525Ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate収率 67.5%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a suspensin of magnesium chloride (1.46 g) in tetrahydrofuran (10 ml) was added a solution of ethyl 3-oxo-4-phenylbutanoate (2.0 g) in tetrahydrofuran (10 ml) and the mixture was cooled to 0° C., then pyridine (2.5 ml) was added. The mixture was stirred at 20° C. for 30 minutes, then a solution of 4-fluorobenzoyl chloride (2.44 g) in tetrahydrofuran (10 ml) was added at 0° C. After stirring at 20° C. for 2 hours, the mixure was partitoned between 0.5N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5) to give ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate (2.15 g) as an oil.

後処理

  1. stirringAfter stirring at 20° C. for 2 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5)

出典と根拠

ORDレコード
ord-6e2cc6132f9e4460b2e12f9e04928393
出典データセット
uspto-grants-2006_12
特許番号
US07153854B2

関連ノート

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