Trichloroacetyl chloride → 2-(Chloromethyl)-3-methylpyridine

HRID 35447

反応式

HRID 35447 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].[Cl:10]C(Cl)(Cl)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:10][CH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 3840573Pyridine, 2,3-dimethyl-, 1-oxide

生成物 1

HCID 130586822-(Chloromethyl)-3-methylpyridine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of 15 g (0.12 mol) of 2,3-dimethylpyridine 1-oxide in 75 ml of chloroform is boiled at reflux and treated as rapidly as possible with 37 ml of trichloroacetyl chloride (it is advantageous to add the acid chloride through the reflux condenser). The reaction mixture is heated under reflux for 2.5 hours, subsequently poured into a mixture of ice and sodium bicarbonate and the resulting solution is washed several times with methylene chloride. The organic phase is dried with sodium sulphate, filtered and concentrated. The residue is chromatographed on silica gel with methylene chloride, the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. The 2-chloromethyl-3-methylpyridine obtained is processed directly.

後処理

  1. temperatureat reflux
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 2.5 hours
  4. washthe resulting solution is washed several times with methylene chloride
  5. dry with materialThe organic phase is dried with sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel with methylene chloride
  9. customthe pressure being produced with nitrogen gas

出典と根拠

ORDレコード
ord-7f7b70aae07c487b8c8cb35b623dcc2d
出典データセット
uspto-grants-1988_08
特許番号
US04766133

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