Toluene → 1,2,6,7-tetrahydro-8H-indeno-(5,4-B)-furan-8-ylidene acetonitrile

HRID 420901노트

반응식

HRID 420901 반응식
C1(C)C=CC=CC=1.[CH2:8]1[CH2:12][O:11][C:10]2[CH:13]=[CH:14][C:15]3[CH2:16][CH2:17][C:18](=O)[C:19]=3[C:9]1=2.[C:21]([CH2:23]P(=O)(OCC)OCC)#[N:22].C[O-].[Na+]>CO.O>[CH2:8]1[CH2:12][O:11][C:10]2[CH:13]=[CH:14][C:15]3[CH2:16][CH2:17]/[C:18](=[CH:23]\[C:21]#[N:22])/[C:19]=3[C:9]1=2

참가 물질

7

반응물 4

HCID 1140TolueneHCID 75676Diethyl (cyanomethyl)phosphonateHCID 10942334Sodium MethoxideHCID 111376161,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

생성물 1

HCID 118303811,2,6,7-tetrahydro-8H-indeno-(5,4-B)-furan-8-ylidene acetonitrile수율 84.4%

시약·촉매·용매 2

HCID 962Water촉매HCID 887Methanol용매

실험 절차

To a solution of toluene (184 g), 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (8.5 g, 48.9 mmol) and diethyl cyanomethylphosphonate (10.4 g, 58.7 mmol) was added dropwise 28% sodium methoxide solution in methanol (11.3 g) over 1 hr under ice-cooling, and reacted for 4 hrs. To the reaction solution was added dropwise water (85 μg), and warmed, then the layers were separated. The organic layer was washed with water, and filtered to remove dusts under pressurization. The organic layer was concentrated under reduced pressure, and to the residue was added methanol and concentrated under reduced pressure to substitute the solvent. After stirring for 1 hr under heating with reflux, the solution was cooled and matured for 1 hr. The crystallization solution was filtered, and the crystals were dried under reduced pressure to give title compound (amount 8.1 g, yield 84.4%).

후처리

  1. temperaturecooling
  2. customreacted for 4 hrs
  3. temperaturewarmed
  4. customthe layers were separated
  5. washThe organic layer was washed with water
  6. filtrationfiltered
  7. customto remove dusts under pressurization
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. additionto the residue was added methanol
  10. concentrationconcentrated under reduced pressure
  11. temperatureunder heating
  12. temperaturewith reflux
  13. temperaturethe solution was cooled
  14. waitmatured for 1 hr
  15. filtrationThe crystallization solution was filtered
  16. customthe crystals were dried under reduced pressure

출처 및 근거

ORD 기록
ord-71450a7f3fd7416abdf312eb7d30bee7
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097737B2

반응 노트

불러오는 중…