Methyl iodide → 2-Methoxy-3-methyl-5-(trifluoromethyl)pyridine

HRID 2106798ノート

反応式

HRID 2106798 の反応式
Br[C:2]1[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH2:14]([Li])CCC.CI.[Cl-].[NH4+]>CCOCC>[CH3:13][O:12][C:3]1[C:2]([CH3:14])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 148370183-Bromo-2-methoxy-5-(trifluoromethyl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 111168552-Methoxy-3-methyl-5-(trifluoromethyl)pyridine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
20 °C

実験手順

A solution of 5.12 g (0.020 mol) of 3-bromo-2-methoxy-5-(trifluoromethyl)pyridine in 60 ml of ether was cooled to -70° C. and blanketed with nitrogen. A solution containing 0.021 mole of butyl lithium (8.4 ml of 2.5 M) was added slowly with stirring keeping the temperature below about -65° C. and the mixture allowed to react for another 30 min. Methyl iodide (0.62 ml, 0.01 mol) was added to the mixture and stirring continued at -70° C. for about 30 min. The mixture was allowed to warm to about 20° C. and was then poured onto a mixture of ice and saturated aqueous ammonium chloride. The organic layer that formed was recovered. The aqueous layer was extracted with ether and the extract added to the organic layer. The combined organic materials were dried over sodium sulfate and concentrated by evaporation under reduced pressure. The residue was distilled to obtain 2.1 g (54 percent of theory) of the title compound as a colorless oil boiling at 67°-69° C. at 24 mm pressure. The proton nmr spectrum was consistent with the assigned structure.

後処理

  1. additionwas added slowly
  2. customthe temperature below about -65° C.
  3. customto react for another 30 min
  4. stirringstirring
  5. customThe organic layer that formed
  6. customwas recovered
  7. extractionThe aqueous layer was extracted with ether
  8. additionthe extract added to the organic layer
  9. dry with materialThe combined organic materials were dried over sodium sulfate
  10. concentrationconcentrated by evaporation under reduced pressure
  11. distillationThe residue was distilled

出典と根拠

ORDレコード
ord-7a018f1b02f94af1a977bcc8af2baaeb
出典データセット
uspto-grants-1990_06
特許番号
US04931452

反応ノート

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