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Tetrahydrofuran → (2'-Fluoro-5'-(methyloxy)-2-(2-methylpropyl)-1,1'-biphenyl-4-yl) methanol

HRID 404359
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HRID 404359 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](OC)=[O:17])=[CH:12][C:11]=1[CH2:20][CH:21]([CH3:23])[CH3:22].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[CH2:20][CH:21]([CH3:23])[CH3:22]
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참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706197Methyl 2'-fluoro-5'-(methyloxy)-2-(2-methylpropyl)-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57706573(2'-Fluoro-5'-(methyloxy)-2-(2-methylpropyl)-1,1'-biphenyl-4-yl) methanol수율 100.2%

실험 절차

To a stirred solution of T23.5 (0.293 g, 0.9 mmol) in THF (5 mL, 0.9 mmol) at 0° C. was added LAH in THF (2 mL, 2 mmol, 1.0M). The reaction was stirred for one hour and then 1N NaOH(aq) was added to quench the mixture. The reaction was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-20% EtOAc in hexanes) to yield T23.6 as a colorless oil (0.260 g, 97% yield).

후처리

  1. customto quench the mixture
  2. extractionThe reaction was extracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-81de502019574c088600ba41a4418d15
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748462B2

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