t-Butyl bromide → 2-Isopropyl-3-(1-hydroxy-2,2-dimethylpropyl)pyrazolo[1,5-a]pyridine

HRID 483086ノート

反応式

HRID 483086 の反応式
[Mg].[C:2](Br)([CH3:5])([CH3:4])[CH3:3].[CH:7]([C:10]1[C:18]([CH:19]=[O:20])=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1)([CH3:9])[CH3:8].[Cl-].[NH4+]>CCOCC.C1C=CC=CC=1>[CH:7]([C:10]1[C:18]([CH:19]([OH:20])[C:2]([CH3:5])([CH3:4])[CH3:3])=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1)([CH3:9])[CH3:8]

参加物

7

反応物 4

HCID 10485t-Butyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 143032672-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde

生成物 1

HCID 133917102-Isopropyl-3-(1-hydroxy-2,2-dimethylpropyl)pyrazolo[1,5-a]pyridine収率 52%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a suspension of 1.6 g of magnesium in 10 ml of dry ether was added a solution of 9.3 g of tert. butylbromide in 15 ml of dry ether under stirring. After the addition was completed, the stirring was continued for an hour at room temperature. To the Grignard reagent were added 2.5 g of 2-isopropyl-3-formylpyrazolo[1,5-a]pyridine in 5 ml of dry benzene under stirring. The mixture was stirred for an hour at room temperature and 11 hours at reflux temperature. The reaction mixture was treated with 100 ml of aqueous 20% ammonium chloride solution and extracted with ether. The ether layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was subjected to silica gel column chromatography, eluted with dichloromethane, to give 1.7 g (52%) of pale yellow crystals, mp 95° C.

後処理

  1. additionAfter the addition
  2. waitthe stirring was continued for an hour at room temperature
  3. stirringunder stirring
  4. stirringThe mixture was stirred for an hour at room temperature and 11 hours
  5. temperatureat reflux temperature
  6. extractionextracted with ether
  7. washThe ether layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. washeluted with dichloromethane

出典と根拠

ORDレコード
ord-161c696e45d14edca61a910d1821d2e3
出典データセット
uspto-grants-1986_03
特許番号
US04578392

反応ノート

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