Potassium Hydroxide → 5-Methoxytricyclo[7.2.1.02,7]dodeca-2(7),3,5,10-tetraene

HRID 1244414노트

반응식

HRID 1244414 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:7]3[CH2:15][CH:10]([C:11](=O)[C:12]=2[CH:13]=1)[CH:9]=[CH:8]3.[OH-].[K+].O.NN>C(O)CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:7]3[CH2:15][CH:10]([CH2:11][C:12]=2[CH:13]=1)[CH:9]=[CH:8]3

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 18415737HCID 18415737, 화합물

생성물 1

HCID 184157365-Methoxytricyclo[7.2.1.02,7]dodeca-2(7),3,5,10-tetraene

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

5-Methoxytricyclo[7.2.1.02.7]dodeca-2(7),3,5,10-tetraene-8-one (9.41 g, 47 mmol) and pulverized potassium hydroxide (KOH) (6.17 g, 110 mmol) were warmed in ethylene glycol (50 mL) until solution occurred. The mixture was cooled to rt, treated with hydrazine hydrate (6 mL, 190 mmol) and heated to reflux for 2 hours. The reflux condenser was replaced with a distilling head and distillates were collected from 120-190° C. The distillates were diluted with H2O (100 mL) and extracted with EiOAc (4×40 mL). The organic layer was washed with H2O (4×30 mL), brine (25 mL), dried (MgSO4), filtered and concentrated to an oil (8.2 g, 94%). (TLC 25%EtOAc/hexanes Rf 0.68). 1H NMR (CDCl3) δ 8.92 (d, J=8.0 Hz, 1H), 6.88 (m, 2H), 6.25 (dd, J=5.1,2.5 Hz, 1H), 5.79 (dd, J=5.1,2.4 Hz, 1H), 3.77 (s, 3H), 3.31 (br s, 1H), 3.01-2.94 (2H), 2.56 (d, J=16.5 Hz, 1H), 2.22 (m, 1H), 1.85 (d, J=10.0 Hz, 1H), GCMS m/e 186 (M+).

후처리

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customwere collected from 120-190° C
  4. additionThe distillates were diluted with H2O (100 mL)
  5. extractionextracted with EiOAc (4×40 mL)
  6. washThe organic layer was washed with H2O (4×30 mL), brine (25 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to an oil (8.2 g, 94%)

출처 및 근거

ORD 기록
ord-5f371e7e1dda47b1bdd71eeed03a13f0
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122534B2

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