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

HRID 721985노트

반응식

HRID 721985 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-363e36871d4f498693238f978c177cf2
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138363B2

반응 노트

불러오는 중…