Pyridine → 2-Acetyl-7-acetoxyfluorene

HRID 2416360Notes

Reaction equation

HRID 2416360 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[C:8]([C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16]C(O)=C[CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)(=[O:10])[CH3:9].N1C=CC=CC=1>C1COCC1>[C:8]([C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8219132-Acetyl-7-hydroxyfluorene

Product 1

HCID 226302682-Acetyl-7-acetoxyfluorene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (50 mL) was added to a mixture of 2-acetyl-7-hydroxyfluorene (50 g), pyridine (200 mL) and THF (200 mL) at 28° C. The temperature was elevated slowly up to 61° C. by exothermic heat to obtain a yellow transparent reaction mixture. An organic layer obtained by extracting the mixture with chloroform was washed well in order with 3M-hydrochloric acid, saturated sodium hydrogencarbonate and water, and then dried on anhydrous magnesium sulfate. The solvent was distilled off from this organic layer under reduced pressure, and the resulting residue was purified by means of column chromatography (silica gel, eluting solvent: toluene) and recrystallization (ethanol/ethyl acetate) to obtain 2-acetyl-7-acetoxyfluorene (47.3 g) of colorless crystal. Melting point: 125.5-127.6° C.

Workup

  1. customwas elevated slowly up to 61° C.
  2. temperatureby exothermic heat
  3. customto obtain a yellow transparent reaction mixture
  4. customAn organic layer obtained
  5. extractionby extracting the mixture with chloroform
  6. washwas washed well in order with 3M-hydrochloric acid, saturated sodium hydrogencarbonate and water
  7. dry with materialdried on anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off from this organic layer under reduced pressure
  9. customthe resulting residue was purified by means of column chromatography (silica gel, eluting solvent: toluene) and recrystallization (ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-de7ee652bc864a4585c5c2a2be16e4ac
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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