Benzyl Alcohol → HCID 69139299, compound

HRID 1458009Notes

Reaction equation

HRID 1458009 reaction equation
F[C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18].[CH2:25]([OH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[CH2:25]([O:32][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 311Citric AcidHCID 24758Sodium hydrideHCID 69138392HCID 69138392, compound

Product 1

HCID 69139299HCID 69139299, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 2.35 g (6.77 mmol) portion of ethyl 5,6,7,8-tetrafluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylate was dissolved in 20 ml of toluene and mixed with 0.70 ml (6.77 mmol) of benzyl alcohol. After cooling to 0° C., this was further mixed with 280 mg (6.99 mmol) of 60% sodium hydride which has been suspended in 10 ml of toluene, and the mixture was stirred at the same temperature for 2 hours and then at room temperature for 2 hours. After completion of the reaction, the reaction solution was mixed with 10% citric acid and extracted with chloroform (100 ml×2). The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:1) to yield 1.68 g (57%) of the title compound.

Workup

  1. waitat room temperature for 2 hours
  2. customAfter completion of the reaction
  3. extractionextracted with chloroform (100 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-11f4600c2fd14c5887c9c109cf22f8f2
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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