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

HRID 1463077ノート

反応式

HRID 1463077 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-10bd69adb4094e7dbaa39dfbe39b9b9d
出典データセット
uspto-grants-1984_07
特許番号
US04463081

反応ノート

読み込み中…