1-Methoxy-2-naphthalenemethanol → 1-Methoxynaphthalene-2-carbaldehyde

HRID 1790295ノート

反応式

HRID 1790295 の反応式
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:13][CH3:14].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:14][O:13][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH:2]=[O:1]

参加物

4

反応物 2

HCID 45591511-Methoxy-2-naphthalenemethanolHCID 178418287HCID 178418287、化合物

生成物 1

HCID 131199931-Methoxynaphthalene-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

The product from Step B (4 g, 27.28 mmol) was dissolved in dichloromethane (100 mL) and cooled to 0° C. To this solution was added pyridinium chlorochromate (5.5 g, 25.53 mmol) and the reaction was stirred at this temperature for 1 h. The reaction mixture was washed with 1 M aqueous solution of hydrogen chloride. The organic layer was separated, dried (MgSO4), and concentrated to give an oil, which was purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9): 1H NMR (CDCl3) δ 4.15 (s, 3H, CH3), 7.61 (m, 3H, Ar—H), 7.87 (m, 2H, Ar—H), 8.28 (m, 1H, Ar—H), 10.61 (s, 1H, CHO); MS 191 (M+NH4+).

後処理

  1. washThe reaction mixture was washed with 1 M aqueous solution of hydrogen chloride
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9)

出典と根拠

ORDレコード
ord-c876af2d9b2c4dcc8051aa884d4c2ab1
出典データセット
uspto-grants-2006_07
特許番号
US07071225B2

反応ノート

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