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Ethylene Glycol → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carboxylic acid

HRID 2245947
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인쇄 미리보기

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HRID 2245947 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5](CC#N)=[CH:4][CH:3]=1.Br[CH2:12][CH2:13]Cl.[OH-:15].[Na+].[CH2:17]([OH:20])[CH2:18]O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:18]2([C:17]([OH:20])=[O:15])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 14751282-(6-Chloropyridin-3-yl)acetonitrile

생성물 1

HCID 592163081-(6-Chloropyridin-3-yl)cyclopropane-1-carboxylic acid수율 85%

시약·촉매·용매 1

HCID 66133
Benzyl triethylammonium chloride
촉매

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온도
50 °C

실험 절차

To a stirred mixture of (6-chloropyridin-3-yl)acetonitrile (2.00 g, 0.0131 mol), benzyltriethylammonium chloride (0.2 g, 0.0008 mol), and 1-bromo-2-chloroethane (3.26 mL, 0.0393 mol), was added sodium hydroxide aqueous solution (50%, 3 mL, 0.08 mol) drop-wise at 50° C. The mixture was stirred at 50° C. for 5 h. 1,2-ethanediol (4 mL) was added to the above mixture and stirred at 100° C. overnight. The aqueous layer was acidified to pH ˜1, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated to afford the desired compound (2.2 g, 85%). Analytical LCMS: (M+H)+=198.0.

후처리

  1. stirringstirred at 100° C. overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f7823ac989934a1582d937efc57ddc50
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07683060B2

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