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Ethylene Glycol → 2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridine

HRID 84380
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HRID 84380 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][N:12]=3)[S:10][C:3]=12.[CH2:19](O)[CH2:20][OH:21].[C@@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[O:16]1[CH2:19][CH2:20][O:21][CH:15]1[C:14]1[CH:17]=[CH:18][C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[N:12][CH:13]=1
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참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 131278(R)-camphorsulfonic acidHCID 579196526-(7-Chlorothieno[3,2-b]pyridin-2-yl)nicotinaldehyde

생성물 1

HCID 579195542-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridine수율 89%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A suspension of 136 (2.69 g, 9.79 mmol), ethylene glycol (2.184 mL, 39.2 mmol), and (1R)-(−)-10-camphorsulfonic acid (0.227 g, 0.979 mmol) in toluene (150 mL) was heated to reflux with a Dean-Stark trap. After 3 h, the mixture was cooled down and filtered through celite (while still warm). The filtrate was washed with water, NaHCO3 (aq., sat.), NaOH (aq) and brine. The solution was then dried over MgSO4 and concentrated to afford compound 137 (2.77 g, 89% yield) as an off-white solid. MS (m/z): 319.1 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux with a Dean-Stark trap
  3. temperaturethe mixture was cooled down
  4. filtrationfiltered through celite (
  5. temperaturewhile still warm)
  6. washThe filtrate was washed with water, NaHCO3 (aq., sat.), NaOH (aq) and brine
  7. dry with materialThe solution was then dried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-56a6bf9539c84dc49769b4bebeb634d4
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846927B2

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