Methanol → 4-(Tert-butyl)-2-(5-methylpyridin-2-yl)phenol

HRID 1480614ノート

反応式

HRID 1480614 の反応式
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:18]C)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.CO.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:18])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 867185702-(5-(Tert-butyl)-2-methoxyphenyl)-5-methylpyridine

生成物 1

HCID 1364080894-(Tert-butyl)-2-(5-methylpyridin-2-yl)phenol収率 92.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 2-(5-(tert-butyl)-2-methoxyphenyl)-5-methylpyridine (1.216 g, 4.76 mmol) in dry dichloromethane (50 mL) at 0° C. under nitrogen was added dropwise a solution of boron tribromide in dichloromethane (1.0 M, 9.52 mL, 9.52 mmol) and the reaction mixture stirred at 0° C. to room temperature for 5 hours. The reaction mixture was then re-cooled to 0° C., methanol (50 mL) added dropwise and the mixture then stirred at 40° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, the residue re-dissolved in methanol (100 mL) and re-concentrated to afford a pink solid. Saturated aqueous sodium hydrogen carbonate solution (80 mL) was added and the resulting suspension extracted with ethyl acetate (80 mL). The organic phase separated, washed with water (80 mL) and saturated brine (80 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a yellow syrup. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 15% ethyl acetate in hexanes to give 4-(tert-butyl)-2-(5-methylpyridin-2-yl)phenol (1.062 g, 92% yield) as a yellow syrup.

後処理

  1. stirringthe mixture then stirred at 40° C. for 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue re-dissolved in methanol (100 mL)
  4. concentrationre-concentrated
  5. customto afford a pink solid
  6. extractionthe resulting suspension extracted with ethyl acetate (80 mL)
  7. customThe organic phase separated
  8. washwashed with water (80 mL) and saturated brine (80 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto give a yellow syrup
  13. customThe crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 15% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-35f7f042093f45f185cc9c5312d415ed
出典データセット
uspto-grants-2016_08
特許番号
US09409893B2

反応ノート

読み込み中…