Hexane → (+/-)-(tetrahydro-2H-pyran-4-yl)(4'-(trifluoromethyl)-[1, 1'-biphenyl]-4-yl)methanol

HRID 2173845

반응식

HRID 2173845 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.[O:29]1[CH2:34][CH2:33][CH:32]([CH:35]=[O:36])[CH2:31][CH2:30]1>C1COCC1>[O:29]1[CH2:34][CH2:33][CH:32]([CH:35]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[OH:36])[CH2:31][CH2:30]1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 127123494-Bromo-4'-(trifluoromethyl)biphenylHCID 178418339Butyllithium

생성물 1

HCID 67980970(+/-)-(tetrahydro-2H-pyran-4-yl)(4'-(trifluoromethyl)-[1, 1'-biphenyl]-4-yl)methanol수율 55%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A round bottom flask at −78° C. was charged with 4-bromo-4′-(trifluoromethyl)-1,1′-biphenyl (192 mg, 0.638 mmol) and THF (2.1 mL). nBuLi 2.5M in Hexane (281 μL, 702 mmol) was then added dropwise. The mixture stirred for one hour at −78° C. after which time, tetrahydro-2H-pyran-4-carbaldehyde (86 μL, 0.83 mmol) was added in one portion and mixture stirred for 30 minutes. Reaction mixture warmed up to 0° C. and stirred for an additional hour. Reaction quenched with ammonium chloride solution (aq. sat.) and extracted twice with ethyl acetate. Combined organic layers washed with brine, dried over sodium sulfate, filtered and concentrated to provide the crude oil. Purification by silica gel flash chromatography (MeOH/DCM) to give the title compound as a colorless oil (118 mg, 55.0%). MS (M): 336.

후처리

  1. additionwas added in one portion and mixture
  2. customReaction mixture
  3. stirringstirred for an additional hour
  4. customReaction
  5. customquenched with ammonium chloride solution (aq. sat.)
  6. extractionextracted twice with ethyl acetate
  7. washCombined organic layers washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto provide the crude oil
  12. customPurification by silica gel flash chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-70f73a6491ed4afca35aa55f60826278
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056834B2

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