Sodium hydride → HCID 10705792, compound

HRID 1975320Notes

Reaction equation

HRID 1975320 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]([O:11][CH2:12]COCC)=[O:10].[H][H].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CN(C=O)C.CCCCCC>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][C:5]2([C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:7][CH2:8][C:4]2=[O:3])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 245432NSC57392HCID 178418361HCID 178418361, compound

Product 1

HCID 10705792HCID 10705792, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred suspension of n-hexane-washed sodium hydride (0.94 g, 39.0 mmol, 1.3 eq) there was added a solution of ethoxyethyl 2-oxocyclopentane-carboxylate (4.26 g, 30.0 mmol, 1.0 eq) in DMF (15 ml) at 0° C. The resulting solution was warmed to room temperature and then stirred for 30 min: the solution became orange. After terminal evolution of hydrogen had been confirmed, p-fluorobenzyl bromide (6.80 g, 36.0 m mol, 1.2 eq) was added to the resulting solution at 0° C. The reaction mixture was then warmed to room temperature and stirred overnight.

Workup

  1. temperatureThe reaction mixture was then warmed to room temperature
  2. stirringstirred overnight

Sources & evidence

ORD record
ord-93a9951843764d85be4c1befc527630f
Source dataset
uspto-grants-1994_02
Patent number
US05286737

Reaction notes

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