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Bis(2-chloroethyl) ether → 4-(Pyridin-4-yl)oxane-4-carboxylic acid

HRID 1698352
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HRID 1698352 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([C:8]([OH:10])=[O:9])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:2]=1
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참가 물질

5

반응물 2

HCID 8115Bis(2-chloroethyl) etherHCID 342284-Pyridineacetic acid

생성물 1

HCID 672728394-(Pyridin-4-yl)oxane-4-carboxylic acid

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 14798Sodium Hydroxide용매

반응 조건

온도
60 °C

실험 절차

To a mixture of pyridin-4-yl-acetic acid (930 mg, 6.0 mmol) and bis-(2-chloroethyl)ether 1.1 mL, 9.0 mmol) in 50% NaOH aq. solution (5 mL) is added benzyltriethylammonium chloride (680 mg, 3 mmol). The solution is heated to 60° C. and stirred at the temperature for 2 hours. After cooling down to rt, the aqueous layer is removed and the organic layer is neutralized with sat. NH4Cl aq. and extracted with Et2O. The combined organic phases are washed with H2O and dried over Na2SO4. Concentration under reduced pressure gives the title compound. The material is used in a next step without purification.

후처리

  1. temperatureAfter cooling down to rt
  2. customthe aqueous layer is removed
  3. extractionextracted with Et2O
  4. washThe combined organic phases are washed with H2O
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-0006fce2f1564e3580e01d7c0bd0840e
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163773B2

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