Thionyl Chloride → 2-(1-Chloro-2-methyl-2-nitropropyl)naphthalene

HRID 895868ノート

反応式

HRID 895868 の反応式
[CH3:1][C:2]([N+:16]([O-:18])=[O:17])([CH3:15])[CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)O.S(Cl)([Cl:21])=O>O>[Cl:21][CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)[C:2]([CH3:15])([N+:16]([O-:18])=[O:17])[CH3:1]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 126400842-Methyl-1-(naphthalen-2-YL)-2-nitropropan-1-OL

生成物 1

HCID 223824212-(1-Chloro-2-methyl-2-nitropropyl)naphthalene

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 2-methyl-1-(naphthalen-2-yl)-2-nitropropanol (1.23 g) obtained in Step 3 was added thionyl chloride (3.1 ml), and the resulting mixture was heated under reflux for 1 hr, and stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=93:7). Recrystallization from a solution of n-hexane:ethyl acetate=4:1, yielded title compound (776 mg).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue thus obtained
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed successively with water and saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=93:7)
  10. customRecrystallization from a solution of n-hexane

出典と根拠

ORDレコード
ord-def03630d0f24735a3f0381f9721c955
出典データセット
uspto-grants-2005_07
特許番号
US06916956B2

反応ノート

読み込み中…