Tetrahydrofuran → 4-(3,4,5-Trifluorophenyl)cyclohexane-1-carbaldehyde

HRID 1977548Notes

Reaction equation

HRID 1977548 reaction equation
[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1.CC(C)([O-])C.[K+].[F:35][C:36]1[CH:37]=[C:38]([CH:44]2CCC(=O)[CH2:46][CH2:45]2)[CH:39]=[C:40]([F:43])[C:41]=1[F:42]>O>[F:35][C:36]1[CH:37]=[C:38]([CH:44]2[CH2:26][CH2:25][CH:24]([CH:28]=[O:27])[CH2:46][CH2:45]2)[CH:39]=[C:40]([F:43])[C:41]=1[F:42]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2723798Methoxymethyl-triphenylphosphonium chloride2×HCID 219932844-(3,4,5-Trifluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 190391814-(3,4,5-Trifluorophenyl)cyclohexane-1-carbaldehydeYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dried methoxymethyltriphenylphosphonium chloride (abbreviated as MTP, hereinafter) 25 g (72.9 mmol), THF 300 ml was added, and potassium-t-butoxide 8.2 g (73.1 mmol) was added. The mixture was stirred for about one hour. To the reactant, a THF solution (150 ml) of the above 4-(3,4,5-trifluorophenyl)cyclohexanone 14.8 g (64.9 mmol) was added dropwise, and the mixture was stirred for 2 hours. Water 300 ml was added to the reactant, the product was extracted with toluene. 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 acid 200 ml and THF 200 ml for 5 hours, 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-(3,4,5-trifluorophenyl) cyclohexanecarboaldehyde 10.5 g (43.3 mmol). The yield was 66.7% from 4-(3,4,5-trifluorophenyl) cyclohexanone.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionthe product was extracted with toluene
  3. washThe extract was washed with a sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  7. customThe resulting purified material
  8. stirringwas stirred in mixture solvent of 3N-hydrochloric acid 200 ml and THF 200 ml for 5 hours
  9. extractionthe product was extracted with toluene
  10. washThe extract was washed with a saturated sodium bicarbonate aqueous solution
  11. dry with materialwith water, and dried over anhydrous magnesium sulfate
  12. distillationToluene was distilled off

Sources & evidence

ORD record
ord-c2b1678965a044f3bfd03679003ab7e2
Source dataset
uspto-grants-2001_05
Patent number
US06235355B1

Reaction notes

Loading…