Hydrogen chloride-ethyl acetate → HCID 70873526, compound

HRID 2172201Notes

Reaction equation

HRID 2172201 reaction equation
C(OCC)(=O)C.Cl.COC[O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)=[N:16][CH:17]=1>C(O)C>[F:30][C:28]([F:29])([F:31])[O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][CH2:18][C:15]2[N:16]=[CH:17][C:12]([OH:11])=[CH:13][CH:14]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86709379HCID 86709379, compound

Product 1

HCID 70873526HCID 70873526, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 N hydrogen chloride-ethyl acetate solution (20 ml) was added to an ethanol solution (20 ml) of 5-methoxymethoxy-2-(4-trifluoromethoxybenzyloxymethyl)pyridine (2.3 g) and stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and a sodium hydrogen carbonate aqueous solution was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and dried over sodium sulfate. The result was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1). The result was concentrated to dryness under reduced pressure to afford the title compound as a white solid (2.4 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona sodium hydrogen carbonate aqueous solution was added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution and dried over sodium sulfate
  6. concentrationThe result was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1)
  8. concentrationThe result was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e063b06cb90141dc882136b347ee39d1
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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