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

HRID 1610456ノート

反応式

HRID 1610456 の反応式
[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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22261618HCID 22261618、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9f5e025afb584ecc94ef792b6388f06f
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

反応ノート

読み込み中…