Tetrahydrofuran → HCID 67046600, compound

HRID 1438391Notes

Reaction equation

HRID 1438391 reaction equation
C1COCC1.[C:6]([C:10]1[C:15]([F:16])=[CH:14][C:13]([CH:17]2[CH2:19][CH:18]2[C:20]([O:22]CC)=[O:21])=[CH:12][C:11]=1[F:25])([CH3:9])([CH3:8])[CH3:7].[OH-].[Na+]>CO>[C:6]([C:10]1[C:11]([F:25])=[CH:12][C:13]([CH:17]2[CH2:19][CH:18]2[C:20]([OH:22])=[O:21])=[CH:14][C:15]=1[F:16])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67046967HCID 67046967, compound

Product 1

HCID 67046600HCID 67046600, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a toluene (50 ml) solution of the compound of Example 38C (4.0 g, 20.4 mmol), Co(TPP) (411 mg, 0.61 mmol) and 1-methyl-1H-imidazole (5.0 g, 61.2 mmol), ethyl diazoacetate (3.5 g, 30.6 mmol) was added and the mixture was stirred for 5 minutes at room temperature followed by additional stirring for 2 hours at 80° C. Then, evaporation and purification by silica gel column chromatography, eluting with gradually from hexane to hexane/EtOAc (20:1), gave ethyl 2-(4-tert-butyl-3,5-difluorophenyl)cyclopropanecarboxylate (4.4 g, 76%, trans). To a THF (5 ml) solution of ethyl 2-(4-tert-butyl-3,5-difluorophenyl)cyclopropanecarboxylate (4.4 g, 15.5 mmol), 2M sodium hydroxide aqueous solution (30 ml) and MeOH (30 ml) were added and the mixture was stirred for 1 hour at room temperature. After the reaction was completed, the aqueous layer was extracted, and then acidified with 2M HCl aqueous solution and the whole was extracted with EtOAc, followed by evaporation, to give the title compound (3.48 g, 88%) as white solids.

Workup

  1. extractionthe aqueous layer was extracted
  2. extractionthe whole was extracted with EtOAc
  3. customfollowed by evaporation

Sources & evidence

ORD record
ord-ebf99496142845d7a43e56267276b9e6
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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