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

HRID 474328

반응식

HRID 474328 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-6902af7ba6ec4cafb811af10766cae5d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637526B2

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