Sodium Hydroxide → 4-Bromo-1-indan-5-yloxybutane

HRID 855571

반응식

HRID 855571 반응식
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].[Br:13][CH:14](C)C(Br)C.S([O-])(O)(=O)=O.[C:24]([NH3+])([CH3:27])([CH3:26])C>C(Cl)Cl>[Br:13][CH2:14][CH2:26][CH2:24][CH2:27][O:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3]2

참가 물질

6

반응물 4

HCID 14798Sodium Hydroxide2회HCID 151185-IndanolHCID 215082,3-DibromobutaneHCID 24996679t-Butylammonium hydrogen sulfate

생성물 1

HCID 130589654-Bromo-1-indan-5-yloxybutane

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Indanol (1 g, 7.45 mmol) in NaOH(aq) (5.22 mL, 20.88 mmol, 4 M soln.) was treated with dibromobutane (3.38 mL, 28.3 mmol) and t-butylammoniumhydrogensulfate (catalytic). The solution was placed in a Robbins™ oven for 14 hours at 99° C. Upon cooling, the pH was adjusted to ˜8 with 4 N NaOH. CH2Cl2 was then added and the solution washed with H2O (×2) and brine. The organic layer was dried over MgSO4 and concentrated to an oil. The oil was then dissolved in 4:1 hexane/EtOAc and passed through a plug of silica gel which was then washed with 4:1 hexane/EtOAc. The filtrate was concentrated to afford 4-bromo-1-indan-5-yloxybutane.

후처리

  1. temperatureUpon cooling
  2. washthe solution washed with H2O (×2) and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated to an oil
  5. dissolutionThe oil was then dissolved in 4:1 hexane/EtOAc
  6. washwas then washed with 4:1 hexane/EtOAc
  7. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-a2ce0ed39d2f4bd6a1bce49565ec54c7
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262198B2

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