Ammonium Chloride → 2,2,2-Trifluoro-1-(4-(trifluoromethyl)phenyl)ethan-1-ol

HRID 520264ノート

反応式

HRID 520264 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+].[NH4+].[Cl-]>CO>[F:1][C:2]([F:15])([F:16])[CH:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=1)[OH:4]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 1446832,2,2-Trifluoro-4'-(trifluoromethyl)acetophenoneHCID 4311764Sodium borohydride

生成物 1

HCID 113908862,2,2-Trifluoro-1-(4-(trifluoromethyl)phenyl)ethan-1-ol収率 105.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In a 50 mL two-neck flask, 2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethanone (2.0 g, 8.3 mmol) was dissolved in methanol (8 mL) and sodium borohydride (0.31 g, 8.3 mmol) was added carefully in portions with ice-bath cooling. The resultant colourless solution was stirred at RT for 2 hours and monitored by TLC. Upon the disappearance of all starting material, 5 mL of an aqueous saturated NH4Cl solution was slowly added to the reaction mixture with additional stirring for 10 min. The later was extracted 3 times with 20 mL of EtOAc and the organic fractions were combined and washed with 10 mL of brine, dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to give 2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethanol (2.13 g, quantitative) as a colourless oil which was used with no further purification.

後処理

  1. temperaturecooling
  2. stirringwith additional stirring for 10 min
  3. extractionThe later was extracted 3 times with 20 mL of EtOAc
  4. washwashed with 10 mL of brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-e683e4134cdc44cf945f314276bb5602
出典データセット
uspto-grants-2016_05
特許番号
US09326513B2

反応ノート

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