Hydrochloric Acid → 3-(4-Chloropyrid-2-yl)-3-oxopropionic acid ethyl ester

HRID 721985ノート

反応式

HRID 721985 の反応式
[H-].[Na+].C(O[C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][N:9]=1)=[O:7])C.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16].Cl>CCCCCC.O1CCCC1>[CH2:19]([O:18][C:15](=[O:17])[CH2:16][C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][N:9]=1)=[O:7])[CH3:20]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 130153594-Chloropyridine-2-carboxylic acid ethyl ester

生成物 1

HCID 534046173-(4-Chloropyrid-2-yl)-3-oxopropionic acid ethyl ester収率 88.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
50 °C

実験手順

Under a nitrogen atmosphere, 4 g (approximately 60% dispersion in paraffin oil, about 100 mmol) of sodium hydride are washed twice with 60 ml of n-hexane each time, and then 400 ml of absolute tetrahydrofuran are added. The mixture is heated to 50° C. and, in the course of 2 hours, a solution of 13.36 g (72 mmol) of 4-chloropyridine-2-carboxylic acid ethyl ester and 10.04 g (114 mmol) of ethyl acetate in 60 ml of absolute tetrahydrofuran is added dropwise, during which the mixture begins to boil vigorously. When the exothermic reaction has subsided, stirring is carried out for 12 hours at room temperature to complete the reaction. The yellow suspension is poured into 400 ml of ice-water and rendered neutral with 15% hydrochloric acid, and the solution is concentrated to half its volume. Extraction is then carried out twice with 200 ml of ethyl acetate each time, and the organic extracts are combined, dried (sodium sulfate), filtered and concentrated. 14.5 g of 3-(4-chloropyrid-2-yl)-3-oxopropionic acid ethyl ester are obtained in the form of a light-brown oil, which is used for further syntheses without further purification.

後処理

  1. customWhen the exothermic reaction
  2. customthe reaction
  3. concentrationthe solution is concentrated to half its volume
  4. extractionExtraction
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-363e36871d4f498693238f978c177cf2
出典データセット
uspto-grants-2006_11
特許番号
US07138363B2

反応ノート

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