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Methylene blue cation → Benzofuran

HRID 1799359
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인쇄 미리보기

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HRID 1799359 반응식
O[C:2]1[CH:7]=[C:6](OC)[CH:5]=[C:4]([O:10]C)[C:3]=1[CH:12](SCCC(O)=O)[CH2:13]C(C)C.CC1C=C[C@@H](C(C)C)CC=1.[N+](CC)([O-])=O.[C].[S].CN(C1C=CC2N=C3C(=CC(C=C3)=[N+](C)C)SC=2C=1)C>C1CCCCC1.[N+](C)([O-])=O>[CH:7]1[CH:2]=[C:3]2[CH:12]=[CH:13][O:10][C:4]2=[CH:5][CH:6]=1
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참가 물질

8

반응물 5

HCID 4139Methylene blue cation3회HCID 6587NitroethaneHCID 442482alpha-PHELLANDRENE, (-)-HCID 58835499HCID 58835499, 화합물HCID 178503045HCID 178503045, 화합물

생성물 1

HCID 9223Benzofuran수율 53%

시약·촉매·용매 2

HCID 6375
Nitromethane
용매
HCID 8078Cyclohexane용매2회

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온도
55 °C

실험 절차

Under the condition of 25° C. and 1 atmospheric pressure, 5.2 mg of 3-[1-(2-hydroxy-4,6-dimethoxyphenyl)-3-methylbutylthio] propanoic acid and 7.2 mg of α-phellandrene were added to the solvent system consisting of of 5 mL of cyclohexane, 4 mL of nitroethane and 1 mL of nitromethane contained in a pyrex glass container and dissolved. Further, 264 mg of lithium perchloride (acceleration of carbon-sulfur cleavage reaction along with the photo electron transportation of a sulfur atom progressed by light irradiation to methylene blue and acceleration of inner molecular ring forming reaction) and 2.3 mg of methylene blue were added and dissolved completely. Lithium perchloride and methylene blue were completely dissolved in the lower layer (nitroalkane layer). By heating this solution to 55° C., homogenized completely and under the argon gas flow halogen lamp (visible ray lamp, wave length from 400 nm to 700 nm) was irradiated for 4 hours. After irradiation, by cooling the reaction solution to 25° C., phase separation occurred again (separated solution system). In the lower layer, methylene blue, lithium perchloride, disulfide generated along with the progress of the reaction and un-reacted starting materials were refined. And, in the cyclohexane layer, the reacted product is refined. Yield is 53%.

후처리

  1. dissolutiondissolved
  2. customforming
  3. additionwere added
  4. dissolutiondissolved completely
  5. customwas irradiated for 4 hours
  6. customAfter irradiation
  7. temperatureby cooling the reaction solution to 25° C.
  8. customphase separation
  9. custom(separated solution system)
  10. customIn the lower layer, methylene blue, lithium perchloride, disulfide generated along with the progress of the reaction
  11. customun-reacted

출처 및 근거

ORD 기록
ord-8484c4737b8f488eb12bbb7e0d0e1c9d
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08344103B2

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