Water → HCID 15635485, compound

HRID 2251990Notes

Reaction equation

HRID 2251990 reaction equation
[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]

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 15635484HCID 15635484, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 15635485HCID 15635485, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c401222056084b2d9339e5842b83a215
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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