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

HRID 895868노트

반응식

HRID 895868 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-def03630d0f24735a3f0381f9721c955
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916956B2

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