Triethylamine → 1-p-Tolyl-3-(t-butyldimethylsiloxy)-2-pyrazoline

HRID 1463077노트

반응식

HRID 1463077 반응식
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH2:10][C:9](=[O:12])[NH:8]2)=[CH:3][CH:2]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(N(CC)CC)C>C1(C)C=CC=CC=1.O1CCCC1.CN(C1C=CN=CC=1)C.N12CCCN=C1CCCCC2>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([N:7]2[CH2:11][CH2:10][C:9]([O:12][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[N:8]2)=[CH:5][CH:6]=1

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 19134851-(4-Methylphenyl)pyrazolidin-3-one

생성물 1

HCID 204468861-p-Tolyl-3-(t-butyldimethylsiloxy)-2-pyrazoline수율 98.2%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
30 °C

실험 절차

To a stirred solution under nitrogen of 1-p-tolyl-3-pyrazolidinone (52.8 g, 0.30 mole) in 500 ml toluene and 50 ml anhydrous tetrahydrofuran was added sequentially t-butyl-dimethylsilyl chloride (49.5 g, 0.30 mole), triethylamine (33.0 g, 0.30 mole), 4-(N,N-dimethylamino)pyridine (0.1 g) and 1,8-diazabicyclo[5.4.0]-undec-7-ene (0.1 g). The mixture was refluxed for 3 hours, then cooled to 30° C., and filtered. After the solids were washed with ether, the solvents of the combined filtrate were removed under reduced pressure. The resulting solid was dissolved in 500 ml anhydrous ether and filtered to remove salts. Removal of the solvent of the filtrate yielded 85.6 g (98% yield) of 1-p-tolyl-3-(t-butyldimethylsiloxy)-2-pyrazoline.

후처리

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationfiltered
  3. washAfter the solids were washed with ether
  4. customthe solvents of the combined filtrate were removed under reduced pressure
  5. dissolutionThe resulting solid was dissolved in 500 ml anhydrous ether
  6. filtrationfiltered
  7. customto remove salts
  8. customRemoval of the solvent of the filtrate

출처 및 근거

ORD 기록
ord-10bd69adb4094e7dbaa39dfbe39b9b9d
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04463081

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