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

HRID 1610421ノート

反応式

HRID 1610421 の反応式
[BH4-].[Na+].[O:3]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4]1.Cl>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[O:3]1[CH:7]=[CH:6][C:5]([CH:8]([OH:26])[CH:9]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22262074Ethyl 3-(3-furanyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionate

生成物 1

HCID 86593246ethyl (2RS,3RS)-3-(3-furanyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate収率 98%

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 (16.0 g, 117 mmol) in diethyl ether (250 ml) was added sodium borohydride (8.9 g, 235 mmol) and the mixture was stirred at room temperature for 2 hrs. The insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-(3-furanyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionate (20 g, 58.8 mmol) in diethyl ether (50 ml) and the mixture was stirred at room temperature for 30 min. 1N Hydrochloric acid was added to the reaction solution under ice-cooling for quenching, water (200 ml), 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 to give ethyl (2RS,3RS)-3-(3-furanyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (19.7 g, 98%) 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. customfor quenching
  5. extractionwater (200 ml), and the mixture was extracted with ethyl acetate (300 ml×2)
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-44aa98cf3fa745d6a943f99ddf6e8b09
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

反応ノート

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