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

HRID 712472

反応式

HRID 712472 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7452e675d20641e6b0762bc342aefbf1
出典データセット
uspto-grants-2015_11
特許番号
US09181277B2

関連ノート

読み込み中…