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

HRID 1790295노트

반응식

HRID 1790295 반응식
[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]

참가 물질

4

반응물 2

HCID 45591511-Methoxy-2-naphthalenemethanolHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 131199931-Methoxynaphthalene-2-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-c876af2d9b2c4dcc8051aa884d4c2ab1
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071225B2

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