HCID 10538857, compound → HCID 10514953, compound

HRID 1019058Notes

Reaction equation

HRID 1019058 reaction equation
[Li][CH2:2]CCC.[CH2:6]1[CH2:23][O:22][C:8]([C:11]2[C:12]([O:20][CH3:21])=[C:13]([C:16]([F:19])=[CH:17][CH:18]=2)[CH:14]=O)([CH2:9][CH3:10])[O:7]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.[Cl-].[Na+].O>[CH2:6]1[CH2:23][O:22][C:8]([C:11]2[C:12]([O:20][CH3:21])=[C:13]([C:16]([F:19])=[CH:17][CH:18]=2)[CH:14]=[CH2:2])([CH2:9][CH3:10])[O:7]1

Participants

6

Reactant 2

HCID 10538857HCID 10538857, compoundHCID 178418339Butyllithium

Product 1

HCID 10514953HCID 10514953, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of methyltriphenylphosphonium bromide (14.3 g, 40 mmol) in THF (250 ml) at room temperature and under nitrogen was added 16 ml (40 mmol) of 2.5 M n-BuLi. To the almost obtained solution was then added 3-[1,1-(ethylenedioxy)-propyl]-6-fluoro-2-methoxybenzaldehyde (10 g, 39.5 mmol) in THF (30 ml). The reaction mixture was then stirred at room temperature for 2 h and poured into a mixture of hexanes and brine. The organic phase was washed two times with brine and one time with water. After evaporation of the solvent, the residue was filtered through a funnel filled with alumina (aluminium oxide 90 acc. Brockmann from Merck) and eluting with EtOAc 1 and hexanes 9 in order to remove the formed triphenylphosphonium oxide. Evaporation of the organic solvent gave a residue which was finally purified on silica gel eluting with EtOAc 1 and hexanes 9 to give 6.9 g (70%) of the title compound with a purity of 94.5% as determined by capillary GC.

Workup

  1. washThe organic phase was washed two times with brine and one time with water
  2. customAfter evaporation of the solvent
  3. filtrationthe residue was filtered through a funnel
  4. additionfilled with alumina (aluminium oxide 90 acc. Brockmann from Merck)
  5. washeluting with EtOAc 1 and hexanes 9 in order
  6. customto remove the formed triphenylphosphonium oxide
  7. customEvaporation of the organic solvent
  8. customgave a residue which
  9. customwas finally purified on silica gel eluting with EtOAc 1 and hexanes 9

Sources & evidence

ORD record
ord-6ffb9c0b9b6b442291c2600230f309a2
Source dataset
uspto-grants-2002_11
Patent number
US06486183B1

Reaction notes

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