Water → 6-Allyloxymethyl-2-Pyridinemethanol

HRID 750532

反応式

HRID 750532 の反応式
[N:1]1[C:6]([CH2:7][OH:8])=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:9][OH:10].[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15].O>CN(C=O)C>[CH2:15]([O:8][CH2:7][C:6]1[N:1]=[C:2]([CH2:9][OH:10])[CH:3]=[CH:4][CH:5]=1)[CH:14]=[CH2:13]

参加物

6

反応物 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 709572,6-Pyridinedimethanol

生成物 1

HCID 218747256-Allyloxymethyl-2-Pyridinemethanol収率 24.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2,6-pyridinedimethanol (5.0 g, 35.9 mmol) in DMF (30 mL) at 0° C. was treated with sodium hydride (1.44 g, 35.9 mmol), stirred for 30 min, treated with allyl bromide (3.42 ml, 39.5 mmol), stirred for 16 h at room temperature, poured into water (150 mL), extracted with EtOAc (3×30 mL) and the combined organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; isohexane:EtOAc (3:1 to 1:1)] to give the title compound (1.56 g, 24%) as a colourless oil: NMR δH (400 MHz, CDCl3) 7.69 (1H, t, J 7.5 Hz), 7.37 (1H, d, J 7.5 Hz), 7.13 (1H, d, J 7.5 Hz), 6.04-5.93 (1H, m), 5.38-5.21 (2H, m), 4.74 (2H, d, J 5.0 Hz), 4.65 (2H, s), 4.15-4.09 (2H, m) and 3.76 (1H, t, J 5.0 Hz).

後処理

  1. stirringstirred for 16 h at room temperature
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; isohexane:EtOAc (3:1 to 1:1)]

出典と根拠

ORDレコード
ord-8730424adc474cb6855ec36067c80f5c
出典データセット
uspto-grants-2008_07
特許番号
US07405219B2

関連ノート

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