Sodium hydride → Tert-butyl(4-tert-butyl-3,5-difluorophenoxy)acetate

HRID 2108829노트

반응식

HRID 2108829 반응식
[H-].[Na+].[C:3]([C:7]1[C:12]([F:13])=[CH:11][C:10]([OH:14])=[CH:9][C:8]=1[F:15])([CH3:6])([CH3:5])[CH3:4].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C1COCC1>[C:21]([O:20][C:18](=[O:19])[CH2:17][O:14][C:10]1[CH:9]=[C:8]([F:15])[C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[C:12]([F:13])[CH:11]=1)([CH3:24])([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 670464324-(tert-Butyl)-3,5-difluorophenol

생성물 1

HCID 90843131Tert-butyl(4-tert-butyl-3,5-difluorophenoxy)acetate수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

To a suspension of sodium hydride (75 mg, 1.9 mmol) in THF (5 ml) was added 4-tert-butyl-3,5-difluorophenol (290 mg, 1.6 mmol) at 0° C., followed by stirring for 30 minutes. Then, tert-butyl bromoacetate (370 mg, 1.9 mmol) was added and the mixture was refluxed at 90° C. for 1 hour. The reaction was quenched with saturated ammonium chloride aqueous solution and the product was extracted with EtOAc, washed with brine, dried over magnesium sulfate. Then, filtration, evaporation, and purification through silica gel column chromatography eluting with hexane/EtOAc (20:1 to 4:1) gave the tert-butyl(4-tert-butyl-3,5-difluorophenoxy)acetate (403 mg, 86%). The DCM (2.0 ml) solution of tert-butyl(4-tert-butyl-3,5-difluorophenoxy)acetate (400 mg, 1.34 mmol) and TFA (2.0 ml), was stirred for 1 hour at room temperature. Evaporation gave the residue which was triturated with Hexane to furnish the title compound as a white solid (253 mg, 77%). 1H NMR (300 MHz, CDCl3): δ 1.42 (9H, t, J=2.2 Hz), 4.63 (2H, s), 6.39 (2H, d, J=12.1 Hz). MS (ESI) m/z 243 (M−H)−.

후처리

  1. customThe reaction was quenched with saturated ammonium chloride aqueous solution
  2. extractionthe product was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThen, filtration, evaporation, and purification through silica gel column chromatography
  6. washeluting with hexane/EtOAc (20:1 to 4:1)

출처 및 근거

ORD 기록
ord-7d54f6d518844c10aa281b59b1bc5c55
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514457B2

반응 노트

불러오는 중…