tert-Butanol → HCID 14621979, compound

HRID 2293823Notes

Reaction equation

HRID 2293823 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>ClCl.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

6

Reactant 3

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

Product 1

HCID 14621979HCID 14621979, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

A solution of Dess-Martin periodinane (1.54 gm, 3.63 mmol) in dry CH2 Cl2 (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 (Na2 SO4), 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. customdried (Na2 SO4)
  8. filtrationfiltered
  9. customThe solid residue was chromatographed (Flash, Merck SiO2, 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-6f76fb62c9bd4011adba4a750f12b6f3
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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