Tetrahydrofuran → HCID 21993293, compound

HRID 1977559Notes

Reaction equation

HRID 1977559 reaction equation
CC(C)([O-])C.[K+].[CH2:7]1[CH2:11][O:10][CH2:9][CH2:8]1.[F:12][C:13]1[CH:14]=[C:15]([CH:20]2CCC(=O)[CH2:22][CH2:21]2)[CH:16]=[C:17]([F:19])[CH:18]=1>O>[F:12][C:13]1[CH:14]=[C:15]([CH:20]2[CH2:9][CH2:8][CH:7]([CH:11]=[O:10])[CH2:22][CH2:21]2)[CH:16]=[C:17]([F:19])[CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 177905164-(3,5-Difluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 21993293HCID 21993293, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dried MTP 10.0 g (29.2 mmol), THF 100 ml was added, and potassium-t-butoxide 3.30 g (29.4 mmol) was added. The mixture was stirred for about one hour. To the reactant, a THF solution (50 ml) of the above 4-(3,5-difluorophenyl)cyclohexanone 5.0 g (23.8 mmol) was added dropwise, and the mixture was stirred for 2 hours. Water 150 ml was added to the reactant, the product was extracted with diethylether. The extract was washed with a sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene). The resulting purified material was stirred in mixture solvent of 3N-hydrochloric add 200 ml and acetone 200 ml for 5 hours at room temperature, and the product was extracted with toluene. The extract was washed with a saturated sodium bicarbonate aqueous solution and then with water, and dried over anhydrous magnesium sulfate. Toluene was distilled off to obtain 4-(3,5-difluorophenyl)cyclohexanecarboaldehyde 5.0 g (22.3 mmol). The yield was 93.7% from 4-(3,5-difluorophenyl) cyclohexanone.

Workup

  1. dry with materialTo dried MTP 10.0 g (29.2 mmol), THF 100 ml
  2. additionwas added
  3. stirringthe mixture was stirred for 2 hours
  4. extractionthe product was extracted with diethylether
  5. washThe extract was washed with a sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  9. customThe resulting purified material
  10. stirringwas stirred in mixture solvent of 3N-
  11. additionhydrochloric add 200 ml and acetone 200 ml for 5 hours at room temperature
  12. extractionthe product was extracted with toluene
  13. washThe extract was washed with a saturated sodium bicarbonate aqueous solution
  14. dry with materialwith water, and dried over anhydrous magnesium sulfate
  15. distillationToluene was distilled off

Sources & evidence

ORD record
ord-a9238151ba01430d863a1e0b95afe16e
Source dataset
uspto-grants-2001_05
Patent number
US06235355B1

Reaction notes

Loading…