tert-Butanol → HCID 14780564, compound

HRID 2295211Notes

Reaction equation

HRID 2295211 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[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=[C:37]([CH:45]([CH3:47])[CH3:46])[C:36]=2[CH2:48][OH:49])=[CH:31][CH:30]=1.CCOC(C)=O>C(Cl)Cl.CCOCC.[OH-].[Na+].CCCCCC>[F:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=[C:37]([CH:45]([CH3:47])[CH3:46])[C:36]=2[CH:48]=[O:49])=[CH:31][CH:30]=1

Participants

9

Reactant 4

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 14780563HCID 14780563, compound

Product 1

HCID 14780564HCID 14780564, compoundYield 92%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Dess-Martin periodinane (1.018 gm, 2.40 mmol) was dissolved in dry CH2Cl2 (12 ml), treated with t-butanol (178 mg, 2.40 mmol) and the resulting mixture was stirred at room temperature for 15 minutes. A solution of 4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinemethanol (539 mg, 1.82 mmol) in CH2Cl2 (8 ml) was then added. After 25 minutes, the solution was then diluted with Et2O (40 ml) and 1N NaOH (25 ml), then stirred an additional 5 minutes. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with saturated NaHCO3 and brine, then dried (Na2SO4), filtered and stripped to give a yellow solid. Flash chromatography (Merck SiO2, 40% EtOAc in hexane) gave 4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxaldehyde (491 mg, 92%) as a white solid. Analytically pure material was obtained by recrystallization from hot hexane.

Workup

  1. waitAfter 25 minutes
  2. stirringstirred an additional 5 minutes
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with Et2O
  5. washThe combined organic layers were washed with saturated NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customto give a yellow solid

Sources & evidence

ORD record
ord-48ddf8241e08411ca0af5e6a5c336ce3
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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