m-Chloroperbenzoic acid → 5-Phenyl-2-pyridylmethyl acetate

HRID 350014

반응식

HRID 350014 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1.ClC1C=CC=[C:17]([C:21]([O:23]O)=[O:22])C=1>O1CCCC1>[C:21]([O:23][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][N:3]=1)(=[O:22])[CH3:17]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 767442-Methyl-5-phenylpyridine

생성물 1

HCID 230250605-Phenyl-2-pyridylmethyl acetate수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-methyl-5-phenylpyridine (3.00 g), 3-chloroperbenzoic acid (4.79 g) and tetrahydrofuran (50 ml) was stirred at room temperature overnight, and concentrated. The residue was subjected to silica gel column chromatography to obtain a colorless oily substance from the fraction eluted with tetrahydrofuran. A solution of the resulting colorless oily substance in acetic anhydride (50 ml) was added slowly to acetic anhydride (50 ml) heated at 130° C., which was stirred at 2 hours, and concentrated. The residue was dissolved in ethyl acetate, which was washed with saturated aqueous sodium bicarbonate solution, and with saturated aqueous sodium chloride solution, and then dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain 5-phenyl-2-pyridylmethyl acetate (3.68 g, yield 92%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 71–72° C.

후처리

  1. concentrationconcentrated
  2. customto obtain a colorless oily substance from the fraction
  3. washeluted with tetrahydrofuran
  4. additionA solution of the resulting colorless oily substance in acetic anhydride (50 ml) was added slowly to acetic anhydride (50 ml)
  5. temperatureheated at 130° C.
  6. stirringwhich was stirred at 2 hours
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washwhich was washed with saturated aqueous sodium bicarbonate solution
  10. dry with materialwith saturated aqueous sodium chloride solution, and then dried (MgSO4)
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-695e36304ce24f708b060f7f3d7bafad
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

연결된 노트

불러오는 중…