Diethyl Ether → 2-(4-(Trifluoromethyl)phenyl)-2-propanol

HRID 1482392

反応式

HRID 1482392 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6](C(OC)=O)=[CH:5][CH:4]=1.[CH3:15][Li].C([O:19][CH2:20][CH3:21])C.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:12]=[CH:11][C:6]([C:20]([OH:19])([CH3:21])[CH3:15])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 520447Methyl 4-(trifluoromethyl)benzoateHCID 178418348HCID 178418348、化合物

生成物 1

HCID 27776172-(4-(Trifluoromethyl)phenyl)-2-propanol収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 4-(trifluoromethyl)benzoate (Compound SP825) (37.1 g, 181 mmol) was dissolved in dehydrated THF (90 ml) under a nitrogen atmosphere, a solution of methyl lithium in diethyl ether (1.5 M, 360 ml, 544 mmol) was added dropwise at 0° C. over 2 hours, and the mixture was stirred at room temperature for 30 minutes. A 50% aqueous ammonium chloride solution was slowly added, followed by extraction with ethyl acetate (200 ml×2). This was dried over sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by Silica gel column chromatography (hexane/DCM=100/0→25/75) to afford 2-[4-(trifluoromethyl)phenyl]propan-2-ol (Compound SP824) (84%, 31.0 g).

後処理

  1. extractionfollowed by extraction with ethyl acetate (200 ml×2)
  2. dry with materialThis was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by Silica gel column chromatography (hexane/DCM=100/0→25/75)

出典と根拠

ORDレコード
ord-c957ed52d4004bb994fe6ad0b0c92bcc
出典データセット
uspto-grants-2016_08
特許番号
US09409952B2

関連ノート

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