Succinic anhydride → Succinic acid Fluorenylmethyl Ester

HRID 440452

Reaction equation

HRID 440452 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:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>N1C=CC=CC=1>[C:1]1([CH2:14][O:15][C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[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 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 523071-Fluorenemethanol

Product 1

HCID 69916676Succinic acid Fluorenylmethyl EsterYield 64.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Fluorenylmethanol (0.90 g, 4.5 mmol) and dimethylaminopyridine (50 mg) were dissolved in 10 ml dry pyridine. Succinic anhydride (0.50 g, 5.0 mmol) was added and the solution stirred overnight. The solvent was 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 was acidified to pH 2, extracted with ethyl acetate (2×100 ml), washed with brine, and the solvent removed under reduced pressure. The residue was purified by flash chromatography (ethyl acetate/hexane 2:1 as eluant) to give 0.86 g product (2.9 mmol, 64%). 1H NMR: (CDCl3, 200 MHz) δ7.8-7.26 (8H, m, ArH), 4.43 (2H, d, J=6.5 Hz, CHCH2OCO), 4.23 (1H, t, J=6.5 Hz, CHCH2OCO), 2.70 (4H, s, OCOCH2CH2COO).

Workup

  1. customThe solvent was 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 was purified by flash chromatography (ethyl acetate/hexane 2:1 as eluant)

Sources & evidence

ORD record
ord-99abc67d5cec4c7e907ea4893a023835
Source dataset
uspto-grants-1996_05
Patent number
US05519134

Linked notes

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