tert-Butanol → HCID 21471359, compound

HRID 2293829Notes

Reaction equation

HRID 2293829 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(O)(C)(C)C.[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]=[C:37]([CH3:47])[C:36]=2[CH2:48][OH:49])=[CH:31][CH:30]=1.[OH-].[Na+]>ClCl.C(Cl)Cl.CC#N.CCOCC.CCCCCC.CCOC(C)=O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]=[C:37]([CH3:47])[C:36]=2[CH:48]=[O:49])=[CH:31][CH:30]=1

Participants

10

Reactant 4

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 14460147HCID 14460147, compound

Product 1

HCID 21471359HCID 21471359, compound

Reagents, catalysts & solvents 5

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 24526ChlorineSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of Dess-Martin periodinane (1.04 gm, 2.45 mmol) in dry CH2 Cl2 (12 ml) was treated with t-butanol (182 mg, 2.46 mmol) and stirred at room temperature for 15 minutes. A slurry of 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinemethanol (555 mg, 1.89 mmol) in CH2Cl2 (10 ml) and CH3CN (2 ml) was then added and stirring was continued for 25 minutes. The mixture was diluted with Et2O (50 ml) and poured into 1N NaOH (25 ml) and stirred for 5 minutes. The phases were separated and the organic layer was washed successfully with 1N NaOH, H2O, and brine, then dried (Na2 SO4). Filtration and removal of the solvent afforded a solid. The solid was dissolved in hot hexane/EtOAc and the resulting solution was cooled to 0° C., filtered and stripped to give a residue which was chromatographed (Flash, Merck SiO2, 20% EtOAc in hexane). 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinecarboxaldehyde was obtained as a white solid (458 mg, 83%). Analytically pure material was obtained by recrystallization from hot hexane.

Workup

  1. stirringstirring
  2. waitwas continued for 25 minutes
  3. stirringstirred for 5 minutes
  4. customThe phases were separated
  5. washthe organic layer was washed successfully with 1N NaOH, H2O, and brine
  6. customdried (Na2 SO4)
  7. filtrationFiltration and removal of the solvent
  8. customafforded a solid
  9. temperaturethe resulting solution was cooled to 0° C.
  10. filtrationfiltered
  11. customto give a residue which
  12. customwas chromatographed (Flash, Merck SiO2, 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-f0fc217b89364167b07945e26ebf35ea
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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