Benzyl Bromide → (3-(Benzyloxy)pyridin-2-yl)methanol

HRID 712472

반응식

HRID 712472 반응식
[OH:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCO>[CH2:12]([O:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 841693-Hydroxypyridine-2-methanol

생성물 1

HCID 13217540(3-(Benzyloxy)pyridin-2-yl)methanol수율 65%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 3-hydroxy-2-(hydroxymethyl)pyridine (10.00 g) and KOH (7.00 g) in anhydrous EtOH was added benzyl bromide (7.30 mL) at room temperature under stirring. The reaction mixture was heated to reflux for 24 h, then cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH) to give the title compound as a pale yellow solid (7.50 g, 65.00%), HPLC: 95.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 216.4 (M+1); 1H NMR (400 MHz, CDCl3) δ: 4.39 (br s, 1H), 4.82 (s, 2H), 5.11 (s, 2H), 7.16-7.17 (m, 2H), 7.34-7.40 (m, 5H), 8.15-8.17 (m, 1H) ppm.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH)

출처 및 근거

ORD 기록
ord-7452e675d20641e6b0762bc342aefbf1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181277B2

연결된 노트

불러오는 중…