2-(4-Methoxy-2-nitrophenyl)acetic acid → 2-(4-Methoxy-2-nitrophenyl)ethan-1-ol

HRID 1914691

反応式

HRID 1914691 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1

参加物

3

反応物 1

HCID 114131802-(4-Methoxy-2-nitrophenyl)acetic acid

生成物 1

HCID 198355352-(4-Methoxy-2-nitrophenyl)ethan-1-ol収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (4-methoxy-2-nitrophenyl)acetic acid (400 mg; 1.9 mmol; 1 eq) in THF (10 mL) at 0° C. is added slowly under nitrogen borane-tetrahydrofuran complex (4.74 mL; 1 M; 4.7 mmol; 2.5 eq) and the reaction is stirred overnight at room temperature. No conversion is observed. The reaction mixture is heated at 70° C. for 2 h. The reaction is quenched by addition of water and the expected product is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent removed under reduced pressure. The residue obtained is purified by the flash chromatography using cyclohexane/EtOAc (7/3) as eluent to afford 350 mg (94%) of the title compound as a yellow oil. 1H NMR (CDCl3) δ 7.20 (d, J=3.0 Hz, 1H), 7.06 (d, J=8.0 Hz, 1H), 6.85 (dd, J=8.0, 3.0 Hz, 1H), 3.66 (t, J=9.0 Hz, 2H), 3.61 (s, 3H), 2.86 (t, J=9.0 Hz, 2H), 1.88 (br s, 1H). HPLC (max plot) 100%; Rt 2.48 min.

後処理

  1. temperatureThe reaction mixture is heated at 70° C. for 2 h
  2. customThe reaction is quenched by addition of water
  3. extractionthe expected product is extracted with EtOAc
  4. dry with materialThe organic phase is dried over MgSO4
  5. customthe solvent removed under reduced pressure
  6. customThe residue obtained
  7. customis purified by the flash chromatography

出典と根拠

ORDレコード
ord-30011162150b4012ad75e34acfb79ea2
出典データセット
uspto-grants-2013_12
特許番号
US08614215B2

関連ノート

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