Hydrochloric Acid → ethyl(2RS,3RS)-3-hydroxy-3-(4-(phenyloxy)phenyl)-2-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionate

HRID 1610482노트

반응식

HRID 1610482 반응식
[BH4-].[Na+].[O:3]=[C:4]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:24])([F:23])[CH:20]([F:22])[F:21])[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:25]1[CH:26]=[CH:27][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:30]=1)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:24])([F:23])[CH:20]([F:22])[F:21])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22261740Ethyl 3-oxo-3-(4-phenyloxyphenyl)-2-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionate

생성물 1

HCID 22261623ethyl(2RS,3RS)-3-hydroxy-3-(4-(phenyloxy)phenyl)-2-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionate수율 67.3%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of zinc chloride (5.34 g, 39.2 mmol) in diethyl ether (120 ml) was added sodium borohydride (2.97 g, 78.4 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off, and a solution of ethyl 3-oxo-3-(4-phenyloxyphenyl)-2-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionate (9.61 g, 19.6 mmol) in diethyl ether (60 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. Then, water (150 ml) was added and the mixture was extracted with ethyl acetate (200 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 (hexane:ethyl acetate=4:1) to give ethyl (2RS,3RS)-3-hydroxy-3-(4-(phenyloxy)phenyl)-2-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionate (6.50 g, 67%) as a colorless oil.

후처리

  1. filtrationInsoluble 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 (200 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 (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-63dcfbcd0f934ac3a3551949d8b09e6b
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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