Glutaric anhydride → Glutaric Acid Monofluorenylmethyl Ester

HRID 1419637Notes

Reaction equation

HRID 1419637 reaction equation
[C:1]1([CH2:14][OH:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[C:25]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[C:1]1([CH2:14][O:15][C:25](=[O:32])[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7940Glutaric anhydrideHCID 218852-DimethylaminopyridineHCID 523071-Fluorenemethanol

Product 1

HCID 18546647Glutaric Acid Monofluorenylmethyl Ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Fluorenylmethanol (0.90 g, 4.5 mmol) and dimethylaminopyridine (50 mg) are dissolved in 10 ml dry pyridine. Glutaric anhydride (5.0 mmol) is added and the solution stirred overnight. The solvent is removed under reduced pressure, sodium bicarbonate added (50 ml), the solution extracted with ethyl acetate (50 ml), and the organic layer discarded. The aqueous layer is acidified to pH 2, extracted with ethyl acetate (2×100 ml), washed with brine, and the solvent removed under reduced pressure. The residue is purified by flash chromatography to give the product.

Workup

  1. customThe solvent is removed under reduced pressure, sodium bicarbonate
  2. additionadded (50 ml)
  3. extractionthe solution extracted with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. washwashed with brine
  6. customthe solvent removed under reduced pressure
  7. customThe residue is purified by flash chromatography
  8. customto give the product

Sources & evidence

ORD record
ord-94e7596da92c4f6893185f39b36cac7b
Source dataset
uspto-grants-1999_03
Patent number
US05886177

Reaction notes

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