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

HRID 1482392

반응식

HRID 1482392 반응식
[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

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 520447Methyl 4-(trifluoromethyl)benzoateHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 27776172-(4-(Trifluoromethyl)phenyl)-2-propanol수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c957ed52d4004bb994fe6ad0b0c92bcc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409952B2

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