Chloroform → HCID 67069107, compound

HRID 909813Notes

Reaction equation

HRID 909813 reaction equation
FC(F)(F)C(O)=O.C(Cl)(Cl)Cl.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=2)O)[CH:16]=[N:17][CH:18]=1.[SiH](CC)(CC)CC>O>[Br:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15]([CH2:19][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67069111HCID 67069111, compound

Product 1

HCID 67069107HCID 67069107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, trifluoroacetic acid (12.5 mL, 0.162 mol) was added dropwise to a chloroform solution of (5-bromopyridine-3-yl)(4-ethoxyphenyl)methanol (2.5 g, 8.11 mmol) and Et3SiH (5.1 mL, 40.6 mmol) at 4° C. and stirred at room temperature for 2.5 hours. The reaction mixture was added with water and extracted with chloroform. After washed with brine, the organic phase was dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound in a colorless needle form (1.83 g, 77%).

Workup

  1. extractionextracted with chloroform
  2. washAfter washed with brine
  3. dry with materialthe organic phase was dried with anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained
  6. customby evaporating the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-314c543b0ab746b6bbd1321d4d701e36
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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