Potassium Carbonate → 5-Cyclopropylmethoxy-1H-indol

HRID 41063

반응식

HRID 41063 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Br[CH2:12][CH:13]1[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:13]1([CH2:12][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH2:15][CH2:14]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 160545-HydroxyindoleHCID 81503Bromomethylcyclopropane2회

생성물 1

HCID 574369835-Cyclopropylmethoxy-1H-indol

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 7.3 g 5-hydroxy-indole in 130 ml of dry acetone are added 10.5 ml bromomethyl cyclopropane and 22.7 g anhydrous potassium carbonate. The mixture is heated to reflux for 24 h and an additional amount of 5 ml bromomethyl cyclopropane are added. The mixture is heated to reflux for additional 4 days. The mixture is filtered and the solvent is removed under reduced pressure. The residue is dissolved in dichloro methane and washed with an aqueous solution of hydrochloric acid (2 M), 10% aq. NaHCO3 and water. The organic layer is dried and the solvent is removed under reduced pressure. After purification by column chromatography (silica gel; toluene, acetone 95:5), 9.62 g, 94%) of the title compound are obtained as an oil. 1H-NMR (CDCl3): 0.36 (m, 2H, cyclopropyl CH2), 0.64 (m, 2H, cyclopropyl CH2), 1.30 (m, 1H, cyclopropyl CH), 3.83 (d, 2H, J=7.0 Hz, CH2O), 6.45 (s, 1H, aromatic), 6.90 (dd, 1H, aromatic), 7.09-7.27 (m, 3H, aromatic), 8.05 (bs, 1H, NH). 13C-NMR (CDCl3): 3.1 (2 cyclopropyl CH2), 10.4 (cyclopropyl CH), 74.2 (CH2O), 101.2, 101.6, 104.0, 104.6, 149.8 (aromatic)

후처리

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 h
  3. temperatureThe mixture is heated
  4. temperatureto reflux for additional 4 days
  5. filtrationThe mixture is filtered
  6. customthe solvent is removed under reduced pressure
  7. dissolutionThe residue is dissolved in dichloro methane
  8. washwashed with an aqueous solution of hydrochloric acid (2 M), 10% aq. NaHCO3 and water
  9. customThe organic layer is dried
  10. customthe solvent is removed under reduced pressure
  11. customAfter purification by column chromatography (silica gel; toluene, acetone 95:5), 9.62 g, 94%) of the title compound
  12. customare obtained as an oil

출처 및 근거

ORD 기록
ord-6920e4434f3d4db69bd1d676b22b48e8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530493B2

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