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

HRID 2174524노트

반응식

HRID 2174524 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

HCID 8264565-Methoxy-1H-indole-2-carbaldehyde수율 76.5%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d6318bc41ed2484b89d85e79a8c37e44
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061994B1

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