Hydrochloric Acid → HCID 58092710, compound

HRID 1807700Notes

Reaction equation

HRID 1807700 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH3:21])([O:16][Si](C)(C)C)[C:12]([F:15])([F:14])[F:13])=[N:9][CH:10]=1.Cl>C1COCC1>[F:15][C:12]([F:13])([F:14])[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][N:9]=1)([OH:16])[CH3:21]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 58092765HCID 58092765, compound

Product 1

HCID 58092710HCID 58092710, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.48 g (4.58 mmol) 5-methoxymethoxy-2-(2,2,2-trifluoro-1-methyl-1-trimethylsilanyloxy-ethyl)-pyridine and 5 ml (10 mmol) 2N HCl in 15 ml THF was stirred at room temperature for 2 h. After that the reaction mixture was poured on water and a pH of 1-2 was adjusted by the addition of 2N HCl. The reaction mixture was extracted 2 times with EtOAc. The combinded organic layers were washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 1.06 g of the title compound as an oil (88% pure), which was used in the next step without purification. LCMS (method L): tR=0.88 min, M+H=252.

Workup

  1. additionAfter that the reaction mixture was poured on water
  2. extractionThe reaction mixture was extracted 2 times with EtOAc
  3. washThe combinded organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e454aadf79844cdfa069f58bab52ba16
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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