2,5-Difluorobenzaldehyde → HCID 23114690, compound

HRID 2080474Notes

Reaction equation

HRID 2080474 reaction equation
C([N-]C(C)C)(C)C.[Li+].[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=1.[F:21][C:22]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=1[CH:24]=[O:25].C(=O)(O)[O-].[Na+]>CCCCCC.O.O1CCCC1.CCCCCCC>[F:21][C:22]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=1[CH:24]([OH:25])[C:18]1[C:17]([F:20])=[CH:16][N:15]=[C:14]([CH:10]2[O:11][CH2:12][CH2:13][O:9]2)[CH:19]=1

Participants

9

Reactant 4

HCID 1376632,5-DifluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 231147942-(1,3-Dioxolan-2-yl)-5-fluoropyridine

Product 1

HCID 23114690HCID 23114690, compoundYield 196.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8900HeptaneSolvent

Procedure

Lithium diisopropylamide (a 1.8M heptane solution, 12 ml, 21.5 mmol) was added to a tetrahydrofuran (100 ml) solution of 2-(1,3-dioxolan-2-yl)-5-fluoropyridine (690 mg, 4.08 mmol) at −75° C. under an argon atmosphere. The resulting mixture was stirred for 2 hours. To the reaction mixture was added dropwise 2,5-difluorobenzaldehyde (2.1 ml, 19.5 mmol), followed by stirring for 2.5 hours. To the reaction mixture were added water and a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with diethyl ether. The extract was washed with brine. The organic layer thus obtained was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=3:1) eluate was concentrated under reduced pressure to give the title compound (2.53 g, 8.03 mmol, 73%) as a white powder.

Workup

  1. stirringby stirring for 2.5 hours
  2. extractionThe resulting mixture was extracted with diethyl ether
  3. washThe extract was washed with brine
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. concentrationethyl acetate (=3:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3fa03ec7b6ae4346ae39a47a92582769
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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