Hydrochloric Acid → ethyl(2RS,3RS)-3-hydroxy-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionate

HRID 1610456노트

반응식

HRID 1610456 반응식
[BH4-].[Na+].[O:3]=[C:4]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl.O>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[OH:3][CH:4]([C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:26][CH:27]=1)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22261618HCID 22261618, 화합물

생성물 1

HCID 22261557ethyl(2RS,3RS)-3-hydroxy-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionate수율 104.2%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of zinc chloride (7.39 g, 54.2 mmol) in diethyl ether (150 ml) was added sodium borohydride (4.11 g, 108.5 mmol), and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off, and a solution of ethyl 3-oxo-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionate (10 g, 25.9 mmol) in diethyl ether (50 ml) was added to the filtrate. The mixture was stirred at room temperature for 30 min. 1N Hydrochloric acid was added to the reaction solution under ice-cooling to quench the reaction. Water (200 ml) was added, and the mixture was extracted with ethyl acetate (300 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give ethyl(2RS,3RS)-3-hydroxy-3-(4-phenoxyphenyl)-2-((4-(trifluoromethyl)phenyl)methyl)propionate (12.0 g, 100%) as a colorless oil.

후처리

  1. filtrationThe insoluble material was filtered off
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. temperaturecooling
  4. customto quench
  5. customthe reaction
  6. extractionthe mixture was extracted with ethyl acetate (300 ml×2)
  7. washThe extract was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-9f5e025afb584ecc94ef792b6388f06f
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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