N-Fluorobenzenesulfonimide → Methyl 2-fluoro-2-pyridin-2-ylpropanoate

HRID 1888160노트

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HRID 1888160 반응식
C(NC(C)C)(C)C.[Li].[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17].[F:21]N(S(C1C=CC=CC=1)(=O)=O)S(C1C=CC=CC=1)(=O)=O>O1CCCC1>[F:21][C:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=1)([CH3:20])[C:16]([O:18][CH3:19])=[O:17]

참가 물질

5

반응물 3

HCID 588007N-FluorobenzenesulfonimideHCID 45051747Lithium diisopropylamineHCID 54595201Methyl 2-(pyridin-2-yl)propanoate

생성물 1

HCID 66881466Methyl 2-fluoro-2-pyridin-2-ylpropanoate수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

To a stirred, cooled (−78° C.) solution of 5.00 mL (10.0 mmol) of a 2.0 M solution of lithium diisopropylamine in tetrahydrofuran under an atmosphere of nitrogen was added a solution of 1.5 g (9.1 mmol) of methyl 2-pyridin-2-yl-propanoate in 4.0 mL of anhydrous THF. The reaction mixture was allowed to stir for 10 min then warmed to 0° C. over 30 min. The mixture was then re-cooled to −78° C. and a solution of 3.70 g (11.8 mmol) of N-fluoro-N-(phenylsulfonyl)benzenesulfonamide in 4.0 mL THF was added. The resulting mixture was allowed to warm to ambient temperature and stir for 2 h. The reaction was quenched with 50 mL of a saturated ammonium chloride solution and then extracted with diethyl ether (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by silica gel chromatography eluting with a 0-40% ethyl acetate in hexanes gradient to afford the title compound as a dark oil (1.3 g, 78%). LC-MS: m/z (E/S) 184 (MH)+.

후처리

  1. temperatureThe mixture was then re-cooled to −78° C.
  2. temperatureto warm to ambient temperature
  3. stirringstir for 2 h
  4. customThe reaction was quenched with 50 mL of a saturated ammonium chloride solution
  5. extractionextracted with diethyl ether (3×50 mL)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude residue was purified by silica gel chromatography
  10. washeluting with a 0-40% ethyl acetate in hexanes gradient

출처 및 근거

ORD 기록
ord-32a63da1ed234b4da36c4a1529fc1d5e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501786B2

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