Glutaric anhydride → Glutaric Acid Monofluorenylmethyl Ester

HRID 1279729Notes

Reaction equation

HRID 1279729 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-5147855d78894f538d5cd31cbf67ddd2
Source dataset
uspto-grants-2002_09
Patent number
US06448373B1

Reaction notes

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