tert-Butanol → HCID 21471506, compound

HRID 1720705Notes

Reaction equation

HRID 1720705 reaction equation
C(O)(C)(C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[C:40]([CH2:41][OH:42])=[C:39]([CH:43]([CH3:45])[CH3:44])[CH:38]=[C:37]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:36]=2)=[CH:31][CH:30]=1>CC#N.C(Cl)Cl.CCOCC>[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[C:40]([CH:41]=[O:42])=[C:39]([CH:43]([CH3:45])[CH3:44])[CH:38]=[C:37]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[N:36]=2)=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 6386tert-ButanolHCID 159087TriacetoxyperiodinaneHCID 15099539HCID 15099539, compound

Product 1

HCID 21471506HCID 21471506, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

t-Butanol (175 mg, 2.35 mmol) was added to a stirring solution of Dess-Martin periodinane (1.005 gm, 2.37 mmol) in dry CH3CN (15 ml). After 15 minutes, a solution of 2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinemethanol (582 mg, 1.81 mmol) in CH3CN (9 ml) and CH2Cl2 (3 ml) was added to the mixture and stirring was continued for 40 minutes. The mixture was diluted with Et2O and quenched with 1N NaOH (25 ml). After 25 minutes of rapid mixing, the biphasic mixture was separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed in succession with 1N NaOH, H2O, and brine, then dried (Na2SO4), filtered and stripped to yield a solid residue. The residue was chromatographed (Merck SiO2, 30% hexane in CH2Cl2) to give 2-(4-fluorophenyl)-4-(1-methylethyl)- 6-phenyl-3-pyridinecarboxaldehyde as a white solid (532 mg, 92%). An analytical sample was obtained by recrystallization from a minimum amount of hot hexane.

Workup

  1. waitwas continued for 40 minutes
  2. customquenched with 1N NaOH (25 ml)
  3. waitAfter 25 minutes of rapid mixing
  4. customthe biphasic mixture was separated
  5. extractionthe aqueous layer was extracted with Et2O
  6. washThe combined organic layers were washed in succession with 1N NaOH, H2O, and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customto yield a solid residue
  10. customThe residue was chromatographed (Merck SiO2, 30% hexane in CH2Cl2)

Sources & evidence

ORD record
ord-bc6d26558f6e4ccfa236030fbaee618f
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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