3,4-dihydro-2H-pyran → N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline

HRID 356224

반응식

HRID 356224 반응식
[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:11][CH2:12][O:13][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 80803,4-dihydro-2H-pyranHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 516892Sodium BicarbonateHCID 18941473N-Ethyl-N-(beta-hydroxyethyl)-4-bromoaniline

생성물 1

HCID 18941483N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
70 °C

실험 절차

14.7 g (60.3 mmols) of N-ethyl-N-(2-hydroxyethyl)-4-bromoaniline, 90 ml of chloroform, 10.68 ml (2.0-fold equivalent weight) of 3,4-dihydro-2H-pyran and 0.76 g (0.05-fold equivalent weight) of pyridine p-toluenesulfonate were mixed, and the mixture obtained was heated at 70° C. for 1.5 hours in an atmosphere of argon. Thereafter, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution obtained, which was then extracted with chloroform (200 ml×2). The organic layer thus formed was washed with a saturated aqueous sodium hydrogencarbonate solution, which was then dried with anhydrous magnesium sulfate and thereafter concentrated. The residue thus obtained was purified by silica gel column chromatography (developing system: chloroform) to obtain 18.90 g of N-ethyl-N-[2-(tetrahydropyran-2-yl)oxyethyl]-4-bromoaniline (yield: quantitative; a colorless oily liquid).

후처리

  1. customthe mixture obtained
  2. customobtained
  3. extractionwhich was then extracted with chloroform (200 ml×2)
  4. customThe organic layer thus formed
  5. washwas washed with a saturated aqueous sodium hydrogencarbonate solution, which
  6. dry with materialwas then dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (developing system: chloroform)

출처 및 근거

ORD 기록
ord-b2c959a9a8bd4a0dac1f7aab1d432dec
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834575

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