Boron trifluoride → 5-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-3-(4-tolyl)-1,2,4-oxadiazole

HRID 2259815노트

반응식

HRID 2259815 반응식
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](Cl)=[O:15])[CH:5]=[CH:4][C:3]1=2.[CH3:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](=[N:25]O)[NH2:24])=[CH:21][CH:20]=1.B(F)(F)F>O1CCOCC1>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[O:15][N:25]=[C:23]([C:22]4[CH:27]=[CH:28][C:19]([CH3:18])=[CH:20][CH:21]=4)[N:24]=3)[CH:5]=[CH:4][C:3]1=2

참가 물질

5

반응물 3

HCID 6356Boron trifluorideHCID 209113N'-Hydroxy-4-methylbenzenecarboximidamideHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride

생성물 1

HCID 147265445-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-3-(4-tolyl)-1,2,4-oxadiazole수율 30.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

8.0 g (30 millimoles) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl chloride and 4.5 g (30 millimoles) of 4-methylbenzamidoxime in 250 ml of dioxane were refluxed for 1 hour. 1 ml of boron trifluoride dietherate were added and refluxing was continued for a further 4 hours. The mixture was allowed to cool, poured onto ice/water and extracted with methylene chloride. The organic phase was washed several times with water, dried over magnesium sulfate and evaporated down. The oily residue was purified by column chromatography (silica gel; n-heptane+0.5% of ethyl acetate), and the crude product obtained from the first fractions was recrystallized from methanol to give 3.2 g of the title compound of melting point 106°-109° C.

후처리

  1. temperaturerefluxing
  2. temperatureto cool
  3. additionpoured onto ice/water
  4. extractionextracted with methylene chloride
  5. washThe organic phase was washed several times with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated down
  8. customThe oily residue was purified by column chromatography (silica gel; n-heptane+0.5% of ethyl acetate)
  9. customthe crude product obtained from the first fractions
  10. customwas recrystallized from methanol

출처 및 근거

ORD 기록
ord-4ea41058d2764a579c6256b99bed2671
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05475017

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