Ethyl bromoacetate → Ethyl 9-fluorenyloxyacetate

HRID 1729245Notes

Reaction equation

HRID 1729245 reaction equation
[H-].[Na+].[CH:3]1[C:15]2[CH:14]([OH:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[CH:3]1[C:15]2[CH:14]([O:16][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 74318Fluoren-9-ol

Product 1

HCID 19011665Ethyl 9-fluorenyloxyacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.8 g of sodium hydride (60% dispersion in mineral oil) was added over 5 minutes under ice-cooling to a solution of 3.64 g of 9-fluorenol and 3 ml of ethyl bromoacetate in 40 ml of N,N-dimethylformamide. After stirring for 50 minutes, the reaction mixture was poured into ice-cold 5% HCl and extracted with ether. The organic layer was washed with a saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by a silica gel column chromatography (eluting solution: methylene chloride-hexane) to give 2.28 g of ethyl 9-fluorenyloxyacetate.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with a saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by a silica gel column chromatography (eluting solution: methylene chloride-hexane)

Sources & evidence

ORD record
ord-08c37652103149928cbd1ee0f0658bea
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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