Cesium carbonate → Ethyl 2-ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanoate

HRID 1183990노트

반응식

HRID 1183990 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]1([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([OH:19])[CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:21][CH2:22][C:23]([CH2:33][CH3:34])([S:29]([CH3:32])(=[O:31])=[O:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1.C(OCC)(=O)C>[CH2:22]([C:23]([S:29]([CH3:32])(=[O:30])=[O:31])([CH2:33][CH2:34][N:16]1[CH:17]=[CH:18][C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:14][C:15]1=[O:19])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:21]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 5987864-Phenylpyridin-2-olHCID 86671954Ethyl 4-bromo-2-ethyl-2-(methylsulfonyl)butanoate

생성물 1

HCID 67248458Ethyl 2-ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanoate수율 20%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
55 °C

실험 절차

Cesium carbonate (0.71 g, 2.2 mmol, 4.0 equiv) was added to a solution of the 4-phenylpyridin-2-ol (0.10 g, 0.58 mmol, 1.05 equiv) and ethyl 4-bromo-2-ethyl-2-(methylsulfonyl)butanoate (0.17 g, 0.55 mmol, 1.0 equiv) in tetrahydrofuran (5 mL). The resulting mixture was heated to 55° C. and allowed to stir for 3 days. The reaction was diluted with ethyl acetate (20 mL), filtered through a pad of Celite, and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (4:1-0:1 heptane/ethyl acetate) to provide a light yellow oil (43 mg, 20%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.15 (t, J=7.42 Hz, 3H) 1.33 (t, J=7.13 Hz, 3H) 2.07-2.19 (m, 1H) 2.26-2.36 (m, 1H) 2.44 (ddd, J=14.89, 11.18, 4.98 Hz, 1H) 2.59-2.71 (m, 1H) 3.15 (s, 3H) 4.19-4.37 (m, 4H) 6.45 (dd, J=7.03, 1.56 Hz, 1H) 6.72-6.78 (m, 1H) 7.38-7.48 (m, 4H) 7.53-7.60 (m, 2H).

후처리

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by flash chromatography on silica gel (4:1-0:1 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-7d93d8a5393b4842ba713ab15420c9a9
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664401B2

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