(5-methoxy-1H-indol-2-yl)methanol → 5-Methoxy-1H-indole-2-carbaldehyde

HRID 2174524ノート

反応式

HRID 2174524 の反応式
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2>CCOC(C)=O.O=[Mn]=O>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3]([CH:2]=[O:1])=[CH:11]2

参加物

4

反応物 1

HCID 10535294(5-methoxy-1H-indol-2-yl)methanol

生成物 1

HCID 8264565-Methoxy-1H-indole-2-carbaldehyde収率 76.5%

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 8857Ethyl Acetate溶媒

実験手順

Compound 425 (100 mg, 0.56 mmol) and MnO2 (490 mg, 5.6 mmol) in EtOAc (5 mL) were heated to reflux for 24 h. The mixture was filtered over Celite, and the filtrate was concentrated in vacuo and purified by chromatography (0% to 10% EtOAc/hexanes) to yield a pale-yellow powder (75 mg, 76%): mp 143-144° C. (lit.58 140-141° C.). TLC Rf 0.28 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 9.81 (s, 1H), 9.05 (s, 1H), 7.36-7.34 (d, 1H, J=12 Hz), 7.20-7.19 (m, 1H), 7.12-7.11 (d, 1H, J=6 Hz), 7.09-7.07 (dd, 1H, J1=9 Hz, J2=2.5 Hz), 3.86 (s, 3H). 13C NMR (150 MHz, CDCl3) δ 181.8, 155.0, 136.3, 133.4, 127.7, 119.4, 114.15, 113.36, 102.8, 55.7. Elemental analysis calculated for C10H9NO2: C, 68.56; H, 5.18; N, 8.00. Found: C, 68.42; H, 5.34; N, 7.85.

後処理

  1. temperatureto reflux for 24 h
  2. filtrationThe mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified by chromatography (0% to 10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-d6318bc41ed2484b89d85e79a8c37e44
出典データセット
uspto-grants-2015_06
特許番号
US09061994B1

反応ノート

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