Potassium Hydroxide → 5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

HRID 741675

반응식

HRID 741675 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[OH-].[K+].[OH:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:3][CH:4]=1

참가 물질

8

반응물 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 693532,5-DibromopyridineHCID 762881-Pyrrolidineethanol

생성물 1

HCID 105881665-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2,5-dibromopyridine (15.0 g, 63.3 mmol), powdered KOH (6.39 g, 114 mmol), 1-(2-hydroxyethyl)pyrrolidine (14.58 g, 126.6 mmol), and 18-crown-6 (300 mg, 1.14 mmol) in dry toluene (100 mL) was heated to 70° C. for 1 h. The solution was cooled to room temperature and water and EtOAc were added. The organic layer was washed with water and brine. The solution was dried (MgSO4), filtered, and concentrated in vacuo. Short path distillation (153° C. @0.1 mmHg) provided the title compound as a colorless oil which solidified upon cooling (14.9 g, 87%). 1H NMR (250 MHz, CDCl3): δ 8.15 (d, J=2.4 Hz, 1H), 7.65 (dd, J=2.4, 8.4 Hz, 1H), 6.67 (d, J=8.4 Hz, 1H), 4.38 (t, J=5.8 Hz, 2H), 2.84 (t, J=5.8 Hz, 2H), 2.62 (m, 4H), 1.82 (m, 4H).

후처리

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. distillationShort path distillation (153° C. @0.1 mmHg)

출처 및 근거

ORD 기록
ord-308f1b4524564f079a73b0c28238ef41
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552412

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