Hexane → 2-Acetyl-6-(((tert-butyldimethylsilyl)oxy)methyl)pyridine

HRID 2218950

반응식

HRID 2218950 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[N:3]=1.CCCCCC.[Li]CCCC.[CH3:28][C:29](N(C)C)=[O:30]>CCOCC.C1COCC1>[C:29]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[N:3]=1)(=[O:30])[CH3:28]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 31374DimethylacetamideHCID 11483477Pyridine, 2-bromo-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-HCID 178418339Butyllithium

생성물 1

HCID 597709522-Acetyl-6-(((tert-butyldimethylsilyl)oxy)methyl)pyridine

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-Bromo-6-(((tert-butyldimethylsilyl)oxy)methyl)pyridine (1.59 g, 5.26 mmol) in a mixture of ether, hexane and THF (2:1:1, 105 mL) was added n-BuLi (3.29 mL, 5.26 mmol, 1.6 M in hexane solution) dropwise at −78° C. during 5-10 min. To the resulting dark brown solution was dropped anhydrous DMA (0.74 mL, 7.89 mmol) at the same temperature. The reaction mixture was stirred for 30 min and then quenched with water (8 mL) and extracted with EtOAc. The organic layer was washed with water and brine and dried over MgSO4. After purification by column chromatography on silica gel (hexane/EtOAc 98:2) 0.78 g (56%) of the title compound as an oil were obtained. 1H NMR (CDCl3) δ 7.95 (d, 1H, J=7.5 Hz, H-3), 7.88 (t, 1H, J=7.6 Hz, H-4), 7.73 (t, 1H, J=7.6 Hz, H-5), 4.93 (s, 2H, CH2), 2.75 (s, 3H, CH3), 1.03 (s, 9H, (CH3)3C), 0.20 (s, 6H, (Me)2Si); 13C NMR (CDCl3) δ 200.8 (CO), 161.4 (C-6), 153.0 (C-2), 139.4 (C-4), 124.0 (C-5), 118.0 (C-3), 66.4 (CH2), 26.3 ((CH3)3C), 18.8 ((CH3)3C), -4.96 ((Me)2Si).

후처리

  1. customquenched with water (8 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customAfter purification by column chromatography on silica gel (hexane/EtOAc 98:2) 0.78 g (56%) of the title compound as an oil
  6. customwere obtained

출처 및 근거

ORD 기록
ord-4af98cd9957c417b8ae94fdec38ce77e
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414036B2

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