tert-Butanol → HCID 14621979, compound

HRID 1720692Notes

Reaction equation

HRID 1720692 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]([CH:47]([CH3:49])[CH3:48])[C:36]=2[CH2:50][OH:51])=[CH:31][CH:30]=1>C(Cl)Cl>[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]([CH:47]([CH3:49])[CH3:48])[C:36]=2[CH:50]=[O:51])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 159087TriacetoxyperiodinaneHCID 14460148HCID 14460148, compound

Product 1

HCID 14621979HCID 14621979, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Dess-Martin periodinane (1.54 gm, 3.63 mmol) in dry CH2Cl2 (17 ml) was treated with t-butanol (267 mg, 3.60 mmol) and stirred for 15 minutes at room temperature. A solution of 4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinemethanol (895 mg, 2.78 mmol) in CH2Cl2 (12 ml) was then added and stirring was continued 30 minutes, after which time the mixture was quenched by the addition of Et2O (70 ml) and 1N NaOH (35 ml). The biphasic mixture was stirred for 10 minutes and the layers were separated. The organic layer was washed with 1N NaOH, H2O and brine, then dried (Na2SO4), filtered and stripped. The solid residue was chromatographed (Flash, Merck SiO2, 10% EtOAc in hexane) to afford pure 4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde (782 mg, 88%) as a white solid. Analytically pure material was obtained by recrystallization of the solid from a minimum amount of hot hexane.

Workup

  1. stirringstirring
  2. waitwas continued 30 minutes
  3. customafter which time the mixture was quenched by the addition of Et2O (70 ml) and 1N NaOH (35 ml)
  4. stirringThe biphasic mixture was stirred for 10 minutes
  5. customthe layers were separated
  6. washThe organic layer was washed with 1N NaOH, H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe solid residue was chromatographed (Flash, Merck SiO2, 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-52208ab0ba8f43169abd68cb8110ffe3
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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