Sodium hydride → HCID 10516025, compound

HRID 1975321Notes

Reaction equation

HRID 1975321 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]([O:11][CH3:12])=[O:10].[H][H].[F:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:17]=1[CH2:18]Br>CN(C=O)C.CCCCCC>[F:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:17]=1[CH2:18][C:5]1([C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:7][CH2:8][C:4]1=[O:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 10516025HCID 10516025, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred suspension of n-hexane-washed sodium hydride (0.58 g, 24 mmol, 1.2 eq), there was added a solution of methyl 2-oxocyclopentanecarboxylate (2.84 g, 20.0 mmol, 1.0 eq) in DMF (20 ml) at 10° C. After the suspension had been heated at room temperature and then stirred for 30 min, the suspension became yellowish. Upon confirmation of the terminal evolution of hydrogen, the resulting solution was again warmed to 10° C. and 2,4-difluorobenzyl bromide (5.38 g, 26.0 mmol, 1.3 eq) was added. The solution was warmed to room temperature and stirred for 2 h. After the terminal reaction had been confirmed by TLC, the resulting solution was poured onto ice-cold water (30 ml) and washed with diethyl ether (100 ml×2).

Workup

  1. temperatureThe solution was warmed to room temperature
  2. stirringstirred for 2 h
  3. customAfter the terminal reaction
  4. additionthe resulting solution was poured onto ice-cold water (30 ml)
  5. washwashed with diethyl ether (100 ml×2)

Sources & evidence

ORD record
ord-d80ad7a97ce84731839d544aef505d6a
Source dataset
uspto-grants-1994_02
Patent number
US05286737

Reaction notes

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