Hydrochloric Acid → Ethyl 2-acetyl-2-chloro-3-(3,4-diethoxyphenyl)propionate

HRID 354682

반응식

HRID 354682 반응식
[Cl:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[CH2:19]Cl)[CH3:14].Cl>CN(C)C=O>[C:8]([C:2]([Cl:1])([CH2:19][C:18]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH3:26])=[C:16]([O:15][CH2:13][CH3:14])[CH:17]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:9])[CH3:10]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 24758Sodium hydrideHCID 24348314-Chloromethyl-1,2-diethoxy-benzene

생성물 1

HCID 13103719Ethyl 2-acetyl-2-chloro-3-(3,4-diethoxyphenyl)propionate수율 71.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

In 100 ml of dry dimethylformamide is dissolved 9.6 g of ethyl 2-chloroacetoacetate, and under ice cooling, 2.32 g of 60% sodium hydride in oil is added. The mixture is stirred at room temperature for 30 minutes. To this mixture are added 12.5 g of 3,4-diethoxybenzyl chloride and 30 ml of dry dimethylformamide, and the mixture is stirred at 70° C. for 2 hours. The mixture is then poured into a mixture of 200 g ice and 50 ml 6N-HCl and extracted with ether. The ethereal layer is washed with water, dried over MgSO4 and distilled to remove the ether. Column chromatography is carried out on the oily residue with 200 g of silica gel, elution being carried out with a 1:4 mixture of ether and n-hexane. The above procedure provides 14.2 g (71.4%) of ethyl 2-acetyl-2-chloro-3-(3,4-diethoxyphenyl)propionate as oil.

후처리

  1. stirringthe mixture is stirred at 70° C. for 2 hours
  2. extractionextracted with ether
  3. washThe ethereal layer is washed with water
  4. dry with materialdried over MgSO4
  5. distillationdistilled
  6. customto remove the ether
  7. washColumn chromatography is carried out on the oily residue with 200 g of silica gel, elution
  8. additionbeing carried out with a 1:4 mixture of ether and n-hexane

출처 및 근거

ORD 기록
ord-b2c185f37de544a8b0eabe5e8f2c0664
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04376777

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