4-Bromobutyric acid → 4-Bromobutanoic Acid 9-Fluorenylmethyl Ester

HRID 329544

Reaction equation

HRID 329544 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:8]1[C:20]2[CH:19]([CH2:21]O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:8]1[C:20]2[CH:19]([CH2:21][O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][Br:1])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 758094-Bromobutyric acidHCID 904669H-Fluorene-9-methanol

Product 1

HCID 145062184-Bromobutanoic Acid 9-Fluorenylmethyl EsterYield 86.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

DDC (6.00 g, 29 mmol) was added in one portion to a cooled solution (0° C.) of 4-bromobutyric acid (5.00 g, 29.9 mmol), 4-(dimethylamino)pyridine (353 mg, 2.9 mmol) and 9-fluorenemethanol (5.63 g, 25 mmol) in CH2Cl2 (150 mL). The mixture was allowed to stand at 4° C. for 18 h, and then filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in EtOAc and the solution washed sequentially with 1N NaHCO3, 1N HCl and H2O. The solution was dried (Na2 -SO4) and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography on silica gel (200 g) using hexane-EtOAc (15:1) as the eluant to give the pure title compound as an oil (7.5 g).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe solution washed sequentially with 1N NaHCO3, 1N HCl and H2O
  5. customThe solution was dried (Na2 -SO4)
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (200 g)

Sources & evidence

ORD record
ord-e881caaf12d945be80405e4641a3e0c4
Source dataset
uspto-grants-1990_01
Patent number
US04891358

Linked notes

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