Dimethylformamide → 4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethyl-benzaldehyde

HRID 1740111ノート

反応式

HRID 1740111 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]([CH2:14][CH3:15])=[C:12]([CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3[O:27][CH2:28][CH3:29])[C:11]([CH2:30][CH3:31])=[N:10]2)=[C:4]([CH3:32])[CH:3]=1.C([Li])CCC.CN(C)[CH:40]=[O:41]>C1COCC1>[CH2:28]([O:27][C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]=1[CH2:16][C:12]1[C:11]([CH2:30][CH3:31])=[N:10][N:9]([C:5]2[C:6]([CH3:8])=[CH:7][C:2]([CH:40]=[O:41])=[CH:3][C:4]=2[CH3:32])[C:13]=1[CH2:14][CH3:15])[CH3:29]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 218373011-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 218373184-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethyl-benzaldehyde収率 112.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazole (0.400 g, 0.81 mmol) in 2.0 ml anhydrous THF was added dropwise to a dry ice-acetone bath cooled solution of n-butyl lithium (2.5 M solution in hexane, 0.358 ml, 0.90 mmol). After stirring 10 minutes, anhydrous dimethylformamide (0.188 ml, 2.43 mmol) was added. After 30 minutes the cooling bath was removed and the mixture was stirred 1 hour. The reaction was quenched by addition of 0.25 ml of a saturated aqueous ammonium chloride solution. After stirring for 5 minutes, the reaction mixture was well-mixed with ethyl acetate/brine (20 ml of each). The aqueous phase was then twice extracted with equal-volume portions of fresh ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated in vacuo to yield an oil (400 mg). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes=1:4 in volume) afforded the title compound (100 mg) as an oil.

後処理

  1. customAfter 30 minutes the cooling bath was removed
  2. stirringthe mixture was stirred 1 hour
  3. customThe reaction was quenched by addition of 0.25 ml of a saturated aqueous ammonium chloride solution
  4. stirringAfter stirring for 5 minutes
  5. additionthe reaction mixture was well-mixed with ethyl acetate/brine (20 ml of each)
  6. extractionThe aqueous phase was then twice extracted with equal-volume portions of fresh ethyl acetate
  7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-add5d8edca0c4be586a8baefbd4da155
出典データセット
uspto-grants-1999_10
特許番号
US05968944

反応ノート

読み込み中…