Sodium Bicarbonate → 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethyl-5-methoxyiminomethyl-pyridine

HRID 973663Notes

Reaction equation

HRID 973663 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([CH:23]([O:47][SiH](C)C)[C:24]1[C:25]([CH:44]([CH3:46])[CH3:45])=[N:26][C:27]([CH:41]([CH3:43])[CH3:42])=[C:28]([CH:37]=[N:38][O:39][CH3:40])[C:29]=1[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)(C)(C)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:44]([C:25]1[C:24]([CH2:23][OH:47])=[C:29]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:28]([CH:37]=[N:38][O:39][CH3:40])=[C:27]([CH:41]([CH3:43])[CH3:42])[N:26]=1)([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 1373311823-(tert.-Butyldimethylsilyloxymethyl)-2,6-diisopropyl-4-(4-fluorophenyl)5-methoxyiminomethyl-pyridine

Product 1

HCID 544628792,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethyl-5-methoxyiminomethyl-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.3 ml (3.3 mmol) of 1 M tetrabutylammonium fluoride solution in tetrahydrofuran is added to a solution of 1.5 g (3.3 mmol) of the compound from Example 1 in 15 ml of absolute tetrahydrofuran and the mixture is stirred at room temperature for 1 hour. Saturated sodium hydrogencarbonate solution is then added to the reaction solution and it is extracted several times with methylene chloride. The combined organic phases are dried (MgSO4), concentrated and then filtered through silica gel.

Workup

  1. extractionis extracted several times with methylene chloride
  2. dry with materialThe combined organic phases are dried (MgSO4)
  3. concentrationconcentrated
  4. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-cb1b702f6efc4b509beff7f55f328f76
Source dataset
uspto-grants-1991_11
Patent number
US05064841

Reaction notes

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