Hydrochloric Acid → Ethyl 2-benzyl-3-(4-methoxyphenyl)propionate

HRID 1709265노트

반응식

HRID 1709265 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>O1CCCC1.O.CN(C)P(=O)(N(C)C)N(C)C.CCCCCC>[CH2:28]([CH:22]([CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 348843Ethyl 3-(4-methoxyphenyl)propanoateHCID 178418339Butyllithium

생성물 1

HCID 15714011Ethyl 2-benzyl-3-(4-methoxyphenyl)propionate

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매HCID 12679Hexamethylphosphoramide용매

실험 절차

9.11 g of diisopropylamine are dissolved in 120 ml of dry tetrahydrofuran, and 54 ml of n-hexane containing n-butyl lithium (10 w/v %) are added dropwise thereto for 15 minutes at -10°-0° C. After the mixture is stirred for 10 minutes, 60 ml of tetrahydrofuran containing 12.5 g of ethyl 3-(4-methoxyphenyl)propionate are added dropwise thereto for 45 minutes at the same temperature. The mixture is stirred for 20 minutes, and 50 ml of tetrahydrofuran containing 16.4 g of benzyl bromide and 9.24 g of hexamethylphosphoric triamide are added dropwise for 10 minutes at -60° C. The mixture is stirred at the same temperature for 2 hours, warmed up to room temperature for one hour under stirring, and stirred at room temperature for an additional one hour. Then, water and 10% hydrochloric acid are added thereto under cooling. The solution is extracted with ethyl acetate, washed, dried, filtered and evaporated to remove the solvent. The residue is purified by flash column chromatography (solvent; n-hexane: ethyl acetate=30:1) to give 9.5 g of ethyl 2-benzyl-3-(4-methoxyphenyl)propionate as colorless oil.

후처리

  1. additionare added dropwise
  2. waitfor 45 minutes at the same temperature
  3. stirringThe mixture is stirred for 20 minutes
  4. stirringThe mixture is stirred at the same temperature for 2 hours
  5. stirringunder stirring
  6. stirringstirred at room temperature for an additional one hour
  7. temperatureunder cooling
  8. extractionThe solution is extracted with ethyl acetate
  9. washwashed
  10. customdried
  11. filtrationfiltered
  12. customevaporated
  13. customto remove the solvent
  14. customThe residue is purified by flash column chromatography (solvent; n-hexane: ethyl acetate=30:1)

출처 및 근거

ORD 기록
ord-fb22d40b7d364371b43c58d9ab50a70d
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04948810

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