Dimethylformamide → HCID 19046983, compound

HRID 1780571Notes

Reaction equation

HRID 1780571 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)[N:15]=1.CN(C)[CH:37]=[O:38]>O1CCCC1.CCCCCC>[F:13][C:14]1[C:19]([CH:37]=[O:38])=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)[N:15]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 179115002-(4-Octyloxyphenyl)-6-fluoropyridineHCID 178418339Butyllithium

Product 1

HCID 19046983HCID 19046983, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2.55 ml (18.2mmol) of diisopropylamine in 30 ml of tetrahydrofuran are stirred at 0° C. with 11.4 ml (18.2mmol) of a 1.6-molar n-butyllithium solution in hexane for one hour. After addition of 170 ml of tetrahydrofuran and cooling to -78° C., 3.64 g (12.1 mmol) of 2-fluoro-6-(4-octyloxyphenyl)pyridine (prepared as described in EXAMPLE 2) in 90 ml of tetrahydrofuran are added dropwise, and the mixture is stirred at -78° C. for 4 hours. 1.86 ml (24.2mmol) of N,N-dimethylformamide are then added dropwise at -78° C., and the reaction mixture is stirred overnight, during which it warms to room temperature. For workup, the mixture is poured onto sodium chloride solution, the resulting mixture is extracted with ether, the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography (silica gel, CH2Cl2) gives 2.20 g of 2-fluoro-3-formyl-6-(4-octyloxyphenyl)pyridine. ##STR62##

Workup

  1. stirringthe reaction mixture is stirred overnight, during which it
  2. customwarms to room temperature
  3. additionFor workup, the mixture is poured onto sodium chloride solution
  4. extractionthe resulting mixture is extracted with ether
  5. washthe organic phase is washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-1cea35c9548d4858ac7ecb960e0909af
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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