4-Fluorobenzaldehyde → 1-(4-Fluorophenyl)-2-(4-(methylthio)phenyl)ethanol

HRID 741683노트

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HRID 741683 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][S:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][Mg]Cl)=[CH:14][CH:13]=1>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:16][C:15]2[CH:19]=[CH:20][C:12]([S:11][CH3:10])=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 680234-FluorobenzaldehydeHCID 178503173HCID 178503173, 화합물

생성물 1

HCID 194267921-(4-Fluorophenyl)-2-(4-(methylthio)phenyl)ethanol수율 24.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of 4-fluorobenzaldehyde (70 mL, 660 mmol) in THF (150 mL) was added to a cold (-78° C.) solution of 4-(methylthio)benzylmagnesium chloride (660 mmol in 1 L of ether) (J.Org. Chem. 42, 19 14, 1977). The mixture was stirred at -78° C. for 10 min then warmed to 0° C. NH4OAc was added and the mixture was extracted with EtOAc. The EtOAc extracts were washed with brine, dried over MgSO4, filtered and concentrated to an oil. Chromatography of the oil on silica gel (eluted with 2.5 % EtOAc/toluene) gave 42 g of the title compound.

후처리

  1. temperaturethen warmed to 0° C
  2. extractionthe mixture was extracted with EtOAc
  3. washThe EtOAc extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil

출처 및 근거

ORD 기록
ord-a619ec0114d4443b99ebce7fa4abbdaf
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552422

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