Sodium Hydroxide → (5'-(Difluoromethyl)-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-yl)methanol

HRID 404373노트

반응식

HRID 404373 반응식
[F:1][CH:2]([F:27])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15](OC)=[O:16])=[CH:11][C:10]=2[C:19]2[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH:20]=2)[CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[F:27][CH:2]([F:1])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=2[C:19]2[C:23]([CH3:24])([CH3:25])[CH2:22][CH2:21][CH:20]=2)[CH:8]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705519Methyl 5'-(difluoromethyl)-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57706435(5'-(Difluoromethyl)-2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-1,1'-biphenyl-4-yl)methanol수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a cooled solution of T34.2 (0.2349 g, 0.6274 mmol) in dry THF (5 mL) at 0° C. was added LAH (1.0 M in THF)(1.3 mL, 1.3 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction (gas evolution occurred). The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-50% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to a colorless oil as T34.3 (166.6 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.47 (2H, m), 7.38 (2H, m), 7.14 (1H, t, J=9.0 Hz), 6.62 (1H, t), 5.50 (1H, td, J=2.4, 1.0 Hz), 4.76 (2H, s), 2.23 (2H, td, J=7.0, 2.3 Hz), 1.74 (3H, m), 0.85 (6H, s).

후처리

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction (gas evolution occurred)
  4. extractionThe resulting solution was extracted three times with EtOAc
  5. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
  6. customthe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-50% EtOAc in hexanes)
  7. additionFractions containing the desired product
  8. concentrationconcentrated to a colorless oil as T34.3 (166.6 mg, 77% yield)

출처 및 근거

ORD 기록
ord-3867c91b02c4450b9a72c45ed747a1f9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748462B2

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