Water → HCID 15635485, 화합물

HRID 2251990노트

반응식

HRID 2251990 반응식
[Li]C(C)(C)C.[CH3:6][Si:7]([CH3:20])([CH3:19])[CH2:8][CH2:9][O:10][CH2:11][O:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.Cl[Si:22]([CH3:25])([CH3:24])[CH3:23].O>CCOCC>[CH3:23][Si:22]([CH3:25])([CH3:24])[C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[O:12][CH2:11][O:10][CH2:9][CH2:8][Si:7]([CH3:20])([CH3:19])[CH3:6]

참가 물질

6

반응물 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 15635484HCID 15635484, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 15635485HCID 15635485, 화합물수율 60%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Add t-BuLi dropwise to a −78° C. solution of 3-(2-trimethylsilanyl-ethoxymethoxy)-pyridine (1.98 g, 8,8 mmol) in Et2O (25 mL, freshly distilled over Na0). After 1 hour, add chlorotrimethylsilane (1.33 mL, 10.5 mmol) dropwise and allow reaction to warm slowly to RT. After 1.5 hours, add water (5 mL) dropwise to quench. Wash with saturated NaHCO3 solution and brine. Dry the combined organic layers over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes to afford the title compound (1.57 g, 60%) as yellow oil. MS(IS) 298 (M+1). TLC: Rf=0.38 (35% EtOAc/hexanes).

후처리

  1. distillationfreshly distilled over Na0)
  2. customreaction
  3. waitAfter 1.5 hours
  4. customto quench
  5. washWash with saturated NaHCO3 solution and brine
  6. dry with materialDry the combined organic layers over MgSO4
  7. concentrationconcentrate
  8. customPurify the residue by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-c401222056084b2d9339e5842b83a215
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320994B2

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