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Lithium Chloride → Ethyl [3-(pyridin-3-yl)phenyl]acetate

HRID 1494137
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HRID 1494137 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=1)(=O)=O.C[Sn](C)C.C[Sn](C)C.FC(F)(F)S(O[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)(=O)=O.[Cl-].[Li+]>O1CCOCC1.CCOCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:37]1[CH:38]=[CH:39][CH:40]=[C:35]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH:36]=1
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참가 물질

8

반응물 4

HCID 433294Lithium ChlorideHCID 6327618HexamethylditinHCID 110315793-Pyridyl TrifluoromethanesulfonateHCID 14986694HCID 14986694, 화합물

생성물 1

HCID 14986695Ethyl [3-(pyridin-3-yl)phenyl]acetate

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 3283Diethyl Ether용매
HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of 2.04 g (6.5 mmol) of ethyl m-(trifluoromethanesulfonyloxy)phenylacetate in 33 mL dioxane is added 1.33 mL (6.5 mmol) hexamethylditin followed by 1.49 g (6.6 mmol) 3-(trifluoromethanesulfonyloxy)-pyridine, 0.827 g (19.5 mmol) lithium chloride and 0.15 g (0.13 mmol) tetrakis-(triphenylphosphine) palladium(0). The mixture is then heated at 90° C. for 62 hours, diluted with ether and washed with 10% ammonium hydroxide followed by water and brine. The organic layer is dried, filtered, evaporated and the residue is purified by flash chromatography using 1:1 ether and hexane as eluent to give ethyl m-(3-pyridyl)phenylacetate; IR (CH2Cl2) 1731 cm-1.

후처리

  1. washwashed with 10% ammonium hydroxide
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue is purified by flash chromatography

출처 및 근거

ORD 기록
ord-4683e9a3b3364fceb1397758c537615f
출처 데이터셋
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05025025

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