1,1'-Carbonyldiimidazole → Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate

HRID 474328

反応式

HRID 474328 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](C)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.[C:24]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:25]C([O-])=O.[K+].[Cl-].[Mg+2].[Cl-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:17])=[C:6]([C:7](=[O:9])[CH2:25][C:24]([O:30][CH2:31][CH3:32])=[O:29])[CH:10]=1

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 820095-Chloro-2-methylbenzoic acidHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

生成物 1

HCID 54012347Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate収率 118%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirring solution of 5-chloro-2-methylbenzoic acid (4.85 g, 28.4 mmol) in tetrahydrofuran (30 mL) was added N,N-carbonyldiimidazole (4.87 g, 30.0 mmol, 1.06 equiv). After 30 minutes, the reaction mixture was added to a suspension of potassium ethyl malonate (11.61 g, 68.22 mmol, 2.40 equiv) and magnesium chloride (3.27 g, 34.3 mmol, 1.21 equiv) in tetrahydrofuran (50 mL). The resultant suspension was heated at 50° C. After hours, the reaction mixture was partitioned between ethyl acetate and water. The organic portion was dried over magnesium sulfate, filtered, and concentrated to provide 8.07 g (118%) of ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate which was used without purification. LCMS (ESI) m+H=241.2

後処理

  1. waitAfter hours
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6902af7ba6ec4cafb811af10766cae5d
出典データセット
uspto-grants-2014_01
特許番号
US08637526B2

関連ノート

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